Hydrochloric Acid → HCID 178499283, compound

HRID 2099677Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:27]2[CH2:32][CH2:31][CH2:30][CH:29]=[CH:28]2)=[CH:8][C:9]=1[N:10]([C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])[CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:4].[BH4-].[Na+].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:27]2[CH2:32][CH2:31][CH2:30][CH:29]=[CH:28]2)=[CH:8][C:9]=1[N:10]([C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[C:18]([C@H:20]1[CH2:21][CH2:22][C@H:23]([CH3:26])[CH2:24][CH2:25]1)=[O:19])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 5-cyclohex-2-enyl-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (40 mg) and MeOH (3 mL) cooled to 0° C. was added NaBH4 (15 mg) in one portion. Reaction was complete in 5 min. HCl (0.1 N, 0.5 mL) was added until it was acidic. It was evaporated and then extracted with DCM, washed with saturated NaHCO3 solution, brine, dried (MgSO4) and evaporated. The crude was purified by chromatography over silica gel (hexane:EtOAc—1:1 as eluent) yielding pure 5-Cyclohex-2-enyl-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (12 mg, 26%) in two steps.

Workup

customReaction
customIt was evaporated
extractionextracted with DCM
washwashed with saturated NaHCO3 solution, brine
dry with materialdried (MgSO4)
customevaporated
customThe crude was purified by chromatography over silica gel (hexane:EtOAc—1:1 as eluent)

Sources & evidence

ORD record: ord-aaf950862d9f45519a87b16830e27131
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569600B2

Reaction notes

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