3-Methoxybenzenethiol → HCID 86751162, compound

HRID 2258030Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[C:10]([O:14][C:15]([NH:17][C:18](=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11]>N1CCCCC1.C(OCC)(=O)C>[C:10]([O:14][C:15]([NH:17][CH:18]([CH:23]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)[S:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:16])([CH3:12])([CH3:13])[CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 0.091 g (0.65 mmol) of 3-methoxy-benzenethiol in 4 drops of piperidine is stirred at room temperature for 5 minutes. A quantity of 0.200 g (0.65 mmol) of 2-tert-butoxycarbonylamino-3-(3-methoxyphenyl)acrylic acid, methyl ester of Example 30 is added and the solution is heated at 60° C. for 24 hours. Ethyl acetate (120 mL) is added and the solution is washed with 3×80 mL of 1N sodium hydroxide and brine (80 mL). After drying (magnesium sulfate), the solution is evaporated and the residue is purified by silica gel chromatography, eluting with 20% ethyl acetate-hexane to give the product as an inseparable mixture of diastereomers; wt 0.26 g (89%);

Workup

washthe solution is washed with 3×80 mL of 1N sodium hydroxide and brine (80 mL)
dry with materialAfter drying (magnesium sulfate)
customthe solution is evaporated
customthe residue is purified by silica gel chromatography
washeluting with 20% ethyl acetate-hexane
customto give the product
additionas an inseparable mixture of diastereomers

Sources & evidence

ORD record: ord-5ce698a558ec4a10bfb5eebe6d4cb31f
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05658943

Reaction notes

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