Triethylamine → [Tert-butoxycarbonyl-(3-chloro-propyl)-amino]-(4-fluoro-phenyl)-acetic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH:12][CH2:13][CH2:14][CH2:15][Cl:16])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.[O:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.O>[CH3:1][O:2][C:3](=[O:17])[CH:4]([N:12]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH2:13][CH2:14][CH2:15][Cl:16])[C:5]1[CH:6]=[CH:7][C:8]([F:11])=[CH:9][CH:10]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of (3-chloro-propylamino)-(4-fluoro-phenyl)-acetic acid methyl ester (14.34 g) in DMF (40 mL) was added BOC2O (11.44 g) followed by triethylamine (15.9 g) and the resultant mixture was stirred overnight at 60° C. A further 0.25 equivalents of BOC2O was added and the reaction mixture was stirred a further 18 hours. The reaction mixture was diluted with EtOAc (200 mL) and water (150 mL), the phases were separated and the organic phase was washed with 0.5 N HCl solution, water, brine and dried over sodium sulfate. Filtration of the drying agent and evaporation of the volatiles in vacuo afforded crude [tert-butoxycarbonyl-(3-chloro-propyl)-amino]-(4-fluoro-phenyl)-acetic acid methyl ester (10.91 g, MS (ES+): 360.1 (MH+)) as a brown oil which was used in the subsequent reaction without further purification.
Workup
- customthe phases were separated
- washthe organic phase was washed with 0.5 N HCl solution, water, brine
- dry with materialdried over sodium sulfate
- filtrationFiltration of the drying agent and evaporation of the volatiles in vacuo
Sources & evidence
- ORD record
- ord-db271ee7537141e6a6c98b51a0027d4e
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124636B2
Reaction notes
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