Trifluoroacetic acid → HCID 178499306, compound

HRID 1694498Notes

Reaction equation

HRID 1694498 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:33]2(O)[CH2:38][CH2:37][CH2:36][CH:35]=[CH:34]2)=[CH:8][C:9]=1[N:10]([C:24]([C@H:26]1[CH2:31][CH2:30][C@H:29]([CH3:32])[CH2:28][CH2:27]1)=[O:25])[C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:13][CH2:12]1)=[O:4].C([SiH](CC)CC)C.FC(F)(F)C(O)=[O:50].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:33]2[CH2:38][CH2:37][CH2:36][CH:35]([OH:50])[CH:34]=2)=[CH:8][C:9]=1[N:10]([C:24]([C@H:26]1[CH2:27][CH2:28][C@H:29]([CH3:32])[CH2:30][CH2:31]1)=[O:25])[C@H:11]1[CH2:12][CH2:13][C@H:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:15][CH2:16]1)=[O:4]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 178499309HCID 178499309, compound

Product 1

HCID 178499306HCID 178499306, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(1-hydroxy-cyclohex-2-enyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[trans-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (48 mg, 0.086 mmol) in DCM (1 mL) was cooled to −50° C. Triethylsilane (43 μl, 0.27 mmol) was added followed by gradual addition of trifluoroacetic acid (total 22 μl, 0.28 mmol) (4 μl to 6 μl every 30 min). The mixture was stirred at −40° C. to −50° C. for 3.5 h. Aqueous NaHCO3 was added and the mixture was allowed to come to room temperature. It was extracted with DCM, washed with brine, dried (MgSO4) and evaporated. The crude was left at room temperature for 2 days and purified by chromatography over silica gel (hexane-EtOAc mixtures) yielding 5-(3-Hydroxy-cyclohex-1-enyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[trans-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (22 mg, 45%).

Workup

  1. customto come to room temperature
  2. extractionIt was extracted with DCM
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. waitThe crude was left at room temperature for 2 days
  7. custompurified by chromatography over silica gel (hexane-EtOAc mixtures)

Sources & evidence

ORD record
ord-ac8fe1f4d2f0478f911e1f8cbc91d5f1
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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