4-Chlorophenyl chloroformate → HCID 58964518, compound

HRID 2069287Notes

Reaction equation

Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:3].[CH3:12][O:13][C:14](=[O:31])[C:15]1[CH:20]=[C:19]([N:21]([C:23](=[O:25])[CH3:24])[CH3:22])[C:18]([C:26]([F:29])([F:28])[F:27])=[CH:17][C:16]=1[NH2:30]>O1CCOCC1>[CH3:12][O:13][C:14](=[O:31])[C:15]1[CH:20]=[C:19]([N:21]([C:23](=[O:25])[CH3:24])[CH3:22])[C:18]([C:26]([F:27])([F:29])[F:28])=[CH:17][C:16]=1[NH:30][C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:3]

Participants

Conditions

Temperature: 80 °C

Procedure

4-chlorophenyl chloroformate (26 mg, 1.1 eq.) is slowly added to a solution of 5-(acetyl-methyl-amino)-2-amino-4-trifluoromethyl-benzoic acid methyl ester (36 mg, 0.12 mmoles) in dioxane (0.2 ml). The solution is stirred at 80° C. for 2 hours. The solution is evaporated to yield 5-(acetyl-methyl-amino)-2-(4-chloro-phenoxycarbonylamino)-4-trifluoromethyl-benzoic acid methyl ester after repeated trituration with hexane. Used tel quel for the next step.

Workup

customThe solution is evaporated

Sources & evidence

ORD record: ord-2537e05657c4472d9725b9a9c64ee5cf
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299085B2

Reaction notes

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