Methyl chloroformate → (S)-benzyl 4-(difluoromethoxy)-2-(methoxycarbonylamino)butanoate

HRID 1185879Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-Benzyl 2-amino-4-(difluoromethoxy)butanoate (116 mg, 0.448 mmol) was dissolved in anhydrous dichloromethane (2.5 mL) and cooled down to 0° C. and TEA (181 mg, 1.79 mmol) and methylchloroformate (51 mg, 0.538 mmol) were added respectively. The mixture was stirred for 30 minutes and then it was stirred at room temperature overnight. The resulting product mixture was quenched with saturated NaHCO3 and extracted with dichloromethane. The organic layer was washed with saturated NH4Cl solution and brine and dried over Na2SO4. The volatiles were removed in vacuo to afford 56 mg (40%) of desired product after column purification.

Workup

stirringit was stirred at room temperature overnight
customThe resulting product mixture was quenched with saturated NaHCO3
extractionextracted with dichloromethane
washThe organic layer was washed with saturated NH4Cl solution and brine
dry with materialdried over Na2SO4
customThe volatiles were removed in vacuo

Sources & evidence

ORD record: ord-f0d4f6d85c0e4f479e305d36d04e3cc8
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669234B2

Reaction notes

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