Water → HCID 178501721, compound

HRID 1694507Notes

Reaction equation

HRID 1694507 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-ee4216dec38c41d1a4bfa6ff50eae443
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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