Trifluoroacetic acid → HCID 54195265, compound

HRID 987062Notes

Reaction equation

HRID 987062 reaction equation
[CH2:1]([NH:8][C:9]([CH2:11][CH:12](O[Si](C(C)(C)C)(C)C)[CH2:13][C:14](=O)[CH2:15][CH2:16][CH:17]1[CH:26]2[C:21](=[CH:22][CH:23]([CH3:34])[CH2:24][CH:25]2[O:27][C:28](=[O:33])[CH:29]([CH3:32])[CH2:30][CH3:31])[CH:20]=[CH:19][CH:18]1[CH3:35])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:8]1[C:9](=[O:10])[CH:11]=[CH:12][CH:13]=[C:14]1[CH2:15][CH2:16][CH:17]1[CH:26]2[C:21](=[CH:22][CH:23]([CH3:34])[CH2:24][CH:25]2[O:27][C:28](=[O:33])[CH:29]([CH3:32])[CH2:30][CH3:31])[CH:20]=[CH:19][CH:18]1[CH3:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69301956HCID 69301956, compound

Product 1

HCID 54195265HCID 54195265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 200 mg (0.32 mmol) 2-methyl-butyric acid 8-[6-benzylcarbamoyl-5-(tert.-butyl-dimethyl-silanyloxy)-3-oxo-hexyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester in 5 ml methylene chloride are added 0.3 g (2.6 mmol) trifluoroacetic acid. After 2 hours at room temperature the reaction mixture is quenched with saturated aqeous sodium bicarbonate. The aqueous phase is separated and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is evaporated. The residue is chromatographed over silica gel (hexane/ethyl acetate 7/3 to 2/3) affording the title compound as a white powder foam. MS (FAB) m/z 480 ([M+Li]+)

Workup

  1. customAfter 2 hours at room temperature the reaction mixture is quenched with saturated aqeous sodium bicarbonate
  2. customThe aqueous phase is separated
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is evaporated
  6. customThe residue is chromatographed over silica gel (hexane/ethyl acetate 7/3 to 2/3)

Sources & evidence

ORD record
ord-38c51f0795fb44a386de423798e9a7f7
Source dataset
uspto-grants-2003_10
Patent number
US06630492B1

Reaction notes

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