Methyl chloroformate → HCID 59446938, compound

HRID 1746785Notes

Reaction equation

[CH:1]1([CH2:4][N:5]([CH2:15][CH2:16][CH3:17])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([OH:14])=O)[CH:7]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OC)=O.[NH2:30][C:31]1[CH:47]=[CH:46][C:34]([CH2:35][S:36]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])(=[O:38])=[O:37])=[CH:33][CH:32]=1>C(Cl)Cl.O>[CH:1]1([CH2:4][N:5]([CH2:15][CH2:16][CH3:17])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([CH2:35][S:36]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])(=[O:38])=[O:37])=[CH:46][CH:47]=3)=[O:14])[CH:7]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) solution of 6-((cyclopropylmethyl)(propyl)amino)pyrimidine-4-carboxylic acid (Intermediate 21, 0.2 g; 0.85 mmol) in DCM (5 ml) was treated with triethylamine (0.13 ml; 0.93 mmol) and methyl chloroformate (0.085 ml; 1.1 mmol). After stirring at 0° C. for 30 minutes, ethyl 3-(4-aminobenzylsulfonyl)propanoate (Intermediate 42, 230 mg; 0.85 mmol) was added. After stirring at 0° C. for 5 minutes and RT for 1 hour water was added and the mixture passed through a hydrophobic frit. The solvent was removed in vacuo and the residue purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as a white solid.

Workup

additionwas added
customThe solvent was removed in vacuo
customthe residue purified by column chromatography (silica)
washeluting with petroleum ether containing
temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record: ord-d9f39a52b20947b88c7c3c560685a6d0
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150519B2

Reaction notes

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