Dimethylamine, hydrochloride → (S)-[2-(4-Amino-phenyl)-1-dimethylcarbamoyl-ethyl]-carbamic acid tert-butylester

HRID 651148Notes

Reaction equation

HRID 651148 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[C:5]([NH:12][C@H:13]([C:22]([OH:24])=O)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]>ClCCl.CN(C)C=O>[C:8]([O:7][C:5](=[O:6])[NH:12][C@H:13]([C:22](=[O:24])[N:3]([CH3:4])[CH3:2])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1)([CH3:9])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 2761482(2S)-3-(4-aminophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

Product 1

HCID 20679220(S)-[2-(4-Amino-phenyl)-1-dimethylcarbamoyl-ethyl]-carbamic acid tert-butylester

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Dimethylamine hydrochloride (2.04 mmol) and Boc-p-amino-L-phenylalanine (1.7 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 4:1 dichloro-methane/dimethylformamide reaction solvent, washed with base only). The product was purified by chromatography on silica gel eluted with 50, 60, 70 and 100% ethyl acetate in hexanes. Yield 226 mg, 42%; HPLC (70/30) 2.45 minutes (100%).

Workup

  1. washwashed with base only)
  2. customThe product was purified by chromatography on silica gel
  3. washeluted with 50, 60, 70 and 100% ethyl acetate in hexanes
  4. customHPLC (70/30) 2.45 minutes (100%)

Sources & evidence

ORD record
ord-d80043dc18314e1685761420946c9821
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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