Benzylamine → ((S)-1-benzylcarbamoyl-ethyl)-carbamic acid tert-butyl ester

HRID 1040529Notes

Reaction equation

HRID 1040529 reaction equation
[N+](C1C=CC([O:10][C:11](=O)[C@@H:12]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:13])=CC=1)([O-])=O.C(=O)([O-])[O-].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[C:18]([O:17][C:15](=[O:16])[NH:14][C@H:12]([C:11](=[O:10])[NH:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:13])([CH3:19])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 19660Carbonate IonHCID 7021877Boc-Ala-ONp

Product 1

HCID 7201376((S)-1-benzylcarbamoyl-ethyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-tert-butoxycarbonylamino-propionic acid 4-nitro-phenyl ester (200 mg, 0.645 mmol) and MP-carbonate (664 mg, 1.93 mmol, Biotage, Part #:800268) in CH2Cl2 (1.5 mL) was added benzylamine (70 mg, 0.645 mmol). The reaction mixture was stirred for 1 h. The reaction mixture was then filtered and concentrated in vacuo to afford ((S)-1-benzylcarbamoyl-ethyl)-carbamic acid tert-butyl ester, m/z 279.4 [M+1]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b3cd442e3124187b24c725cccebcb98
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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