Methanol → HCID 16074975, compound

HRID 1015643Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]([C:34](=[O:43])[C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=2[Cl:42])[C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:21][C:20]=2[C:30]([O:32]C)=[O:31])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O.CO>C1COCC1.CO.O.CC(O)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]([C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:21][C:20]=2[C:30]([OH:32])=[O:31])[C:34](=[O:43])[C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:36]=2[Cl:42])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

4-{[(2,4-Dichloro-benzoyl)-(2-methoxycarbonyl-5-phenyl-thiophen-3-yl)-amino]-methyl}-piperidine-1-carboxylic acid benzyl ester (150 mg, 0.24 mmol) was dissolved in a mixture of THF:MeOH:H2O (3:2:1, 2.4 mL) and treated with LiOH.H2O (29.6 mg, 0.7 mmol). The solution was heated at 55° C. for 2 h. The solvents were removed and the residue was acidified using HCl. The product was extracted with EtOAc and the organic layers were washed with brine and dried. The residue was purified by silica gel column chromatography using EtOAc:MeOH:AcOH as eluent to provide 4-{[(2-Carboxy-5-phenyl-thiophen-3-yl)-(2,4-dichloro-benzoyl)-amino]-methyl}-piperidine-1-carboxylic acid benzyl ester (124 mg, 85% yield).

Workup

customThe solvents were removed
extractionThe product was extracted with EtOAc
washthe organic layers were washed with brine
customdried
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-07366594f6ac4eeea21343982c38f730
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985769B2

Reaction notes

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