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Ammonium Bicarbonate → ethyl (2R)-2-acetylamino-3-(3-cyanophenyl)propanoate

HRID 47727
Notes
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Reaction equation

HRID 47727 reaction equation
[C:1]([NH:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].C(=O)([O-])O.[NH4+]>O.C(#N)C>[C:1]([NH:4][C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14013Ammonium BicarbonateHCID 85797672ethyl (2RS)-2-acetylamino-3-(3-cyanophenyl)propanoate

Product 1

HCID 86584426ethyl (2R)-2-acetylamino-3-(3-cyanophenyl)propanoateYield 47.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

The process is performed as in Example 2, starting with 11.39 g of ethyl (2RS)-2-acetylamino-3-(3-cyanophenyl)propanoate, 17.39 g of ammonium hydrogen carbonate and 0.1 g of α-chymotrypsin in 200 cm3 of water and 70 cm3 of acetonitrile. After stirring for 24 hours at a temperature in the region of 20° C. and an identical work-up, 5.40 g of ethyl (2R)-2-acetylamino-3-(3-cyanophenyl)propanoate are obtained in the form of a beige-colored solid. (Rf=0.76 in a 40/10/20 by volume mixture of n-butanol/acetic acid/water, on a Merck 60F254R silica plate).

Sources & evidence

ORD record
ord-e4dd21c7908148a8aeb2c86ba6a87e89
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699895B2

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes