Isopropyl Acetate → 1,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate

HRID 2301738Notes

Reaction equation

HRID 2301738 reaction equation
C(OC(C)C)(=O)C.[C:8]([O:12][C:13]([NH:15][CH:16]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:17]([OH:20])[CH2:18][Cl:19])=[O:14])([CH3:11])([CH3:10])[CH3:9]>>[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C@H:17]([OH:20])[CH2:18][Cl:19])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

3

Reactant 2

HCID 7915Isopropyl AcetateHCID 4712659(2R,3S)-3-(Tert-butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane

Product 1

HCID 71466451,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate

Procedure

The thus-obtained isopropyl acetate solution was analyzed by HPLC, and it was identified that 3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane (0.57 g) was obtained in a yield of 83%. A ratio of the desired product (2S,3S) and its isomer (2R,3S) formed was (2S,3S):(2R,3S)=83.2:16.8.

Workup

  1. customwas obtained in a yield of 83%

Sources & evidence

ORD record
ord-f2c97f95d37c4186ad1fd5c831dc69b3
Source dataset
uspto-grants-2002_12
Patent number
US06500985B2

Reaction notes

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