Water → HCID 178501721, compound

HRID 1190057Notes

Reaction equation

HRID 1190057 reaction equation
[C:1]1([C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[C:9]([N:15]([C@H:25]3[CH2:30][CH2:29][C@H:28]([OH:31])[CH2:27][CH2:26]3)[C:16]([C@H:18]3[CH2:23][CH2:22][C@H:21]([CH3:24])[CH2:20][CH2:19]3)=[O:17])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[N:32]([C@@H:35]([CH:40]([CH3:42])[CH3:41])[C:36]([O:38][CH3:39])=[O:37])=[C:33]=[O:34].O>C1(C)C=CC=CC=1>[C:1]1([C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[C:9]([N:15]([C@H:25]3[CH2:26][CH2:27][C@H:28]([O:31][C:33](=[O:34])[NH:32][CH:35]([C:36]([O:38][CH3:39])=[O:37])[CH:40]([CH3:42])[CH3:41])[CH2:29][CH2:30]3)[C:16]([C@H:18]3[CH2:23][CH2:22][C@H:21]([CH3:24])[CH2:20][CH2:19]3)=[O:17])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10397066Methyl (S)-(-)-2-Isocyanato-3-methylbutyrateHCID 178461274HCID 178461274, compound

Product 1

HCID 178501721HCID 178501721, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-cyclohex-1-enyl-3-{(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexane-carbonyl)-amino}-thiophene-2-carboxylic acid (20 mg, 0.045 mmol) and methyl (S)-(−)-2-isocyanato-3-methylbutyrate (10 μl, 0.07 mmol) in toluene (1 mL) was stirred at 70° C. for 2 h. It was cooled and water (1 mL) was added. The mixture was stirred at room temperature for one h. It was extracted with EtOAc (50 mL), washed with brine, dried (MgSO4) and evaporated. Pure 5-cyclohex-1-enyl-3-[{trans-4-(1-methoxycarbonyl-2-methyl-propylcarbamoyloxy)-cyclohexyl}-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid was obtained by chromatography over silica gel (hexane-EtOAc mixtures, pure EtOAc and 5% acetone in DCM as eluent) (12.4 mg, 45%).

Workup

  1. temperatureIt was cooled
  2. stirringThe mixture was stirred at room temperature for one h
  3. extractionIt was extracted with EtOAc (50 mL)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c0f757c8973e48b78260ffc15c8f5fbe
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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