Ammonia → 1-Cbz-(S)-azetidine-2-carboxamide

HRID 1430135Notes

Reaction equation

HRID 1430135 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=O.[NH3:19]>CO>[CH2:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C@H:5]1[C:3](=[O:2])[NH2:19])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54265762(2S)-Methyl-1-(benzyloxycarbonyl)azetidine-2-carboxylate

Product 1

HCID 108235791-Cbz-(S)-azetidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-azetidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (2.5 g) and 7M ammonia in methanol (10 ml) is stood at room temperature for 18 hours in a sealed vessel. The reaction mixture is then evaporated to give the title compound as a white solid which is used without further purification. MS M+H 235.1 and M−H 233.1.

Workup

  1. customThe reaction mixture is then evaporated

Sources & evidence

ORD record
ord-2f4d7ed15476489cbeda8157be7959af
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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