Hydrochloric Acid → Methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate

HRID 343952Notes

Reaction equation

[C:1]([NH:9][CH:10]([C:15]1[C:20]([CH3:21])=[CH:19][C:18](S(C(F)(F)F)(=O)=O)=[C:17]([O:29][CH3:30])[CH:16]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(PCCCPC2C=CC=CC=2)C=CC=CC=1.[C]=O.Cl>CN(C)C=O.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([NH:9][CH:10]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:11]([O:13][CH3:14])=[O:12])=[C:17]([O:29][CH3:30])[CH:16]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred mixture of methyl 2-benzamido-2-(3-methoxy-6-methyl-4-trifluoromethylsulphonylphenyl)acetate (0.3 g, 0.65 mmol) triethylamine (0.16 g, 1.6 mmol), palladium acetate (5 mg, 0.022 mmol) and 1,3-diphenylphosphinopropane (9 mg, 0.022 mmol) in dimethyformamide (3 ml) and methanol was saturated with carbon monoxide gas using a bubbler and then heated to 70° C. for 3 hours and overnight at room temperature under an atmosphere of carbon monoxide using a gas filled balloon. The mixture was acidified with aqueous hydrochloric acid (2M) and extracted with ethyl acetate (2×). The combined extracts were washed with a saturated solution of ammonium chloride, dried, filtered and evaporated to a solid. Chromatography on flash silica eluting with diethyl ether-hexane (3:2, 4:1) gave methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate as a white solid.

Workup

additionfilled balloon
extractionextracted with ethyl acetate (2×)
washThe combined extracts were washed with a saturated solution of ammonium chloride
customdried
filtrationfiltered
customevaporated to a solid

Sources & evidence

ORD record: ord-aa94ff5fb5b64809833e4317a26fcf04
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05863947

Reaction notes

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