Benzene → Methyl 1-{[(alpha-Chloroisobutoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

HRID 384550Notes

Reaction equation

[Cl:1][CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH:3]([CH3:5])[CH3:4].[CH:21]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[Cl:1][CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of (93) (1.0 g, 3.3 mmol), benzene (90 mL), and methanol (10 mL) was cooled to 0° C. Trimethylsilyldiazomethane was added slowly at 0° C. until the yellow color persisted. The mixture was stirred at 0° C. for 30 min until the reaction was complete (monitored by TLC). After removing the solvent under reduced pressure, chromatography of the resulting residue on silica gel, eluting with 10% ethyl acetate/hexane gave 760 mg (72%) of the title compound. MS (ESI) m/z 320.24 (M+H+).

Workup

customAfter removing the solvent under reduced pressure, chromatography of the resulting residue on silica gel
washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record: ord-0b7b399b936d4badb1cbfc62ee768f82
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367722B2

Reaction notes

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