Methanol → HCID 178496600, compound

HRID 1694442Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:6][C:7]([CH:28]2[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][CH2:29]2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([O:26][CH3:27])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].CO.O.O[Li].O>C1COCC1>[CH3:35][C:31]1([CH3:34])[CH2:30][CH2:29][CH:28]([C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([N:10]([C@H:20]3[CH2:21][CH2:22][C@H:23]([O:26][CH3:27])[CH2:24][CH2:25]3)[C:11]([C@H:13]3[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]3)=[O:12])[CH:8]=2)[CH2:33][CH2:32]1

Participants

Conditions

Temperature: 60 °C

Procedure

5-(4,4-Dimethylcyclohexyl)-3-[(trans-4-methoxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (890 mg, 1.76 mmol) was dissolved in a 3:2:1 mixture of THF:methanol:H2O (50 mL) and treated with a 1N solution of LiOH.H2O (5.29 mL, 5.29 mmol). After stirring for 2 h at 60° C., the reaction mixture was evaporated to dryness and suspended in water. The reaction mixture was acidified to pH 3. After extraction with EtOAc, the organic fraction was washed with water, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CH2Cl2:MeOH (90:10) as eluent affording the 5-(4,4-dimethyl-cyclohexyl)-3-[(trans-4-methoxy-cyclohexyl)-(trans-4-methylcyclohexane-carbonyl)-amino]-thiophene-2-carboxylic acid (535 mg, 58%) as a solid.

Workup

customthe reaction mixture was evaporated to dryness
extractionAfter extraction with EtOAc
washthe organic fraction was washed with water
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-e3713bf7ce574b19a9e3b802bbb89dc7
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158675B2

Reaction notes

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