Methyl chloroformate → HCID 18981005, compound

HRID 482621Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].Cl.[CH3:13][O:14][C:15](=[O:18])[CH2:16][NH2:17].C(N(C(C)C)CC)(C)C.Cl[C:29]([O:31][CH3:32])=[O:30]>>[CH3:32][O:31][C:29]([N:17]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4])[CH2:16][C:15]([O:14][CH3:13])=[O:18])=[O:30]

Participants

Reactant 4

HCID 6586Methyl chloroformate

HCID 68303p-Chlorophenacyl bromide

HCID 81531Diisopropylethylamine

HCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 18981005HCID 18981005, compoundYield 27.8%

Procedure

By substantially following the procedure given in Example 585c using 35 g (150 mmole) of 2-bromo-4'-chloroacetophenone, 20.7 g (160 mmole) of glycine methyl ester hydrochloride, 40.6 g (310 mmole) of diisopropylethyl amine, and 14.2 g (150 mmole) of methyl chloroformate, 12.5 g of the desired compound, an oil, was obtained.

Sources & evidence

ORD record: ord-beef22803f56414fb7e960a7bbd36c03
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05798311

Reaction notes

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