Boc-3-Hydroxy-1-adamantyl-D-glycine

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Cost-effective and customizable Boc-3-Hydroxy-1-adamantyl-D-glycine 361442-00-4 factory

  • Molecular Formula: C17H27NO5
  • Molecular Weight: 325.405
  • Boiling Point: 497.253 °C at 760 mmHg 
  • PKA: 3.93±0.10(Predicted) 
  • Flash Point: 254.53 °C 
  • PSA: 95.86000 
  • Density: 1.296 g/cm3 
  • LogP: 2.68650 

361442-00-4 Relevant articles

Preparation of an amino acid intermediate for the dipeptidyl Peptidase IV inhibitor, saxagliptin, using a modified phenylalanine dehydrogenase

Hanson, Ronald L.,Goldberg, Steven L.,Brzozowski, David B.,Tully, Thomas P.,Cazzulino, Dana,Parker, William L.,Lyngberg, Olav K.,Vu, True C.,Wong, Michael K.,Patel, Ramesh N.

, p. 1369 - 1378 (2007)

The non-proteinogenic amino acid 2-(3-hy...

Synthetic method of saxagliptin intermediate

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Paragraph 0032; 0041-0043; 0052-0053, (2021/11/21)

The invention belongs to the technical f...

A process for preparing hydroxy adamantane glycine derivatives

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Paragraph 0034-0036, (2017/07/14)

The invention aims to provide a novel an...

Intermediates for synthesizing sand Geleg sandbank N-tert-butoxycarbonyl-3-hydroxy-1-adamantyl-D-gly method

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Paragraph 0014; 0028; 0029, (2018/02/04)

The invention discloses a novel method o...

PROCESS FOR PREPARING DIPEPTIDYL PEPTIDASE IV INHIBITORS AND INTERMEDIATES THEREFOR

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Paragraph 0034; 0055; 0087; 0088; 0089; 0090; 0091, (2016/07/27)

A process for preparing an amine of the ...

361442-00-4 Process route

(αS)-α-amino-3-hydroxytricyclo[3.3.1.1<sup>3,7</sup>]decane-1-acetic acid
709031-29-8,709031-30-1

(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7 ]decane-1-acetic acid

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert -butyl dicarbonate

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1<sup>3,7</sup>]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7 ]decane-1-acetic acid

Conditions
Conditions Yield
With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 12h;
98%
With potassium phosphate; In tetrahydrofuran; sodium hydroxide; at 20 ℃; for 2h;
88%
(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; di-tert-butyl dicarbonate; With sodium hydroxide; for 4h; pH=10;
With sulfuric acid; In Isopropyl acetate; water; for 0.0833333 - 0.166667h; pH=2.0 - 8;
88%
With sodium hydroxide; In Isopropyl acetate; at 20 ℃; for 4h; pH=10; Large scale;
88%
With sodium hydroxide; at 20 - 30 ℃; for 12h; Large scale;
87.53%
(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; di-tert-butyl dicarbonate; With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;
With hydrogenchloride; In tetrahydrofuran; ethyl acetate; for 1h; pH=1 - 7;
With sodium hydroxide; at 25 - 30 ℃; for 5h;
15.6 g
N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine

N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1<sup>3,7</sup>]decane-1-acetic acid
361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7 ]decane-1-acetic acid

Conditions
Conditions Yield
With (1R,2S)-2-Amino-1,2-diphenylethanol; In ethyl acetate; at 20 ℃; for 2h; Reflux; Resolution of racemate;
56%
Multi-step reaction with 2 steps
1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate
2: hydrogenchloride / ethyl acetate; water / pH 3
With hydrogenchloride; In water; ethyl acetate;
Multi-step reaction with 2 steps
1: ethanol / 0.08 h / Resolution of racemate; Reflux
2: hydrogenchloride / water; ethyl acetate / pH 2
With hydrogenchloride; In ethanol; water; ethyl acetate;

361442-00-4 Upstream products

  • 361441-97-6
    361441-97-6

    (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7 ]decane-1-acetic acid

  • 709031-29-8
    709031-29-8

    (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7 ]decane-1-acetic acid

  • 24424-99-5
    24424-99-5

    di-tert -butyl dicarbonate

  • 361441-95-4
    361441-95-4

    (S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

361442-00-4 Downstream products

  • 361442-01-5
    361442-01-5

    tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13 '7 ]dec-1-yl)-2-oxoethyl]carbamate

  • 709031-43-6
    709031-43-6

    3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7 ]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

  • 1564265-93-5
    1564265-93-5

    saxagliptin

  • 1564265-94-6
    1564265-94-6

    (S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile

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