Triethylamine → Methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]carbonylamino}propanoate

HRID 585066Notes

Reaction equation

Cl.[NH2:2][CH:3]([CH2:8][OH:9])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>ClCCl>[OH:9][CH2:8][CH:3]([NH:2][C:23]([C:22]1[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:27][CH:26]=1)=[O:24])[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 2-amino-3-hydroxypropanoate hydrochloride (L-serine methyl ester hydrochloride, 1.71 g, 11 mmol) was stirred in dichloromethane (20 ml) at 0° C., and triethylamine (2.79 ml, 20 mmol) added, followed by dropwise addition of 4-trifluoromethylbenzoyl chloride (1.486 ml, 11 mmol). The mixture was stirred at 0° C. for 30 minutes, then partitioned between dichloromethane and water, dried over magnesium sulfate, and filtered. Solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography, to yield methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]carbonylamino}propanoate, a compound of formula (13). B. Preparation of a Compound of Formula (14)

Workup

custompartitioned between dichloromethane and water
dry with materialdried over magnesium sulfate
filtrationfiltered
customSolvent was removed from the filtrate under reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-c55fafae59fa4b5aa3840cec9054dbd7
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930111B2

Reaction notes

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