Acetic Acid → HCID 178499285, compound

HRID 1694503Notes

Reaction equation

HRID 1694503 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[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].C(O)(=O)C.C(OC(=O)C)(=O)C.C([O-])(O)=O.[Na+].[CH3:49][S:50]([CH3:52])=O>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])[C@H:20]1[CH2:25][CH2:24][C@H:23]([O:26][CH2:49][S:50][CH3:52])[CH2:22][CH2:21]1)=[O:4]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178499281HCID 178499281, compound

Product 1

HCID 178499285HCID 178499285, compound

Procedure

To a solution of 5-cyclohex-1-enyl-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (25 mg, 0.054 mmol) in DMSO (0.2 mL) was added a mixture of acetic acid and acetic anhydride (1:5.6) (0.17 mL). After stirring for 1.5 h at room temperature it was held at 40° C. for 5 h. It was cooled to room temperature and stirred for 16 h. The mixture was cooled in ice-bath and NaHCO3 solution was added carefully. It was extracted with ether. The extract was washed with water and brine, dried over MgSO4 and evaporated. Pure 5-cyclohex-1-enyl-3-[(trans-4-methyl-cyclohexanecarbonyl)-(trans-4-methylsulfanylmethoxy-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester was obtained by chromatography over silica gel (hexane:EtOAc=−4:1) (22 mg, 77%).

Workup

  1. waitwas held at 40° C. for 5 h
  2. temperatureIt was cooled to room temperature
  3. stirringstirred for 16 h
  4. temperatureThe mixture was cooled in ice-bath
  5. extractionIt was extracted with ether
  6. washThe extract was washed with water and brine
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-ef70af9e81594de1b83c2dbac157625b
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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