Sodium Chloride → N-[(1S)-1-Cyano-2-phenylethyl]formamide

HRID 351339

Reaction equation

HRID 351339 reaction equation
[CH:1]([O-:3])=O.[Na+].[Cl-].[Na+].C1N(CCCS(O)(=O)=O)CCOC1.[NH2:20][CH:21]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22]#[N:23]>>[CH:1]([NH:20][C@@H:21]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22]#[N:23])=[O:3]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 70807MopsHCID 5613842-Amino-3-phenylpropanenitrileHCID 2723810Sodium Formate

Product 1

HCID 71417709N-[(1S)-1-Cyano-2-phenylethyl]formamide

Procedure

To 27 mL buffer-solution of pH 7.4 (containing 0.1 mg/mL catalase, 6 M sodium formate, 0.25 M sodium chloride and 100 mM MOPS buffer) was added 25 mg PDF and 1.0 g rac-2-amino-3-phenylpropionitrile.HCl-salt. This solution was adjusted to pH 6.7. After 20 h of shaking at ambient temperature the reaction was stopped at 38% conversion. A small amount of the heterogeneous reaction mixture was extracted with CH2Cl2. (S)-2-Formamido-3-phenylpropionitrile with e.e.>99% (HPLC) was isolated from the organic layer. The precipitate in the remaining part of the reaction mixture was filtered yielding (S)-2-formamido-3-phenylpropionitrile (e.e.>99.5%) as a white solid.

Workup

  1. extractionA small amount of the heterogeneous reaction mixture was extracted with CH2Cl2

Sources & evidence

ORD record
ord-83de400408ac43a59be18869b72e0ef3
Source dataset
uspto-grants-2007_02
Patent number
US07183443B2

Linked notes

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