Acetic Acid → HCID 69855632, compound

HRID 2415116Notes

Reaction equation

HRID 2415116 reaction equation
C([Si](C)(C)[O:6][CH:7]([CH2:32][C:33](=[O:36])[NH:34][CH3:35])[CH2:8][C:9](=[O:31])[CH2:10][CH2:11][CH:12]1[CH:21]2[C:16](=[CH:17][CH:18]([CH3:29])[CH2:19][CH:20]2[O:22][C:23](=[O:28])[CH:24]([CH3:27])[CH2:25][CH3:26])[CH:15]=[CH:14][CH:13]1[CH3:30])(C)(C)C.[C:39](O)(=[O:41])C.O.O.O.[F-].C([N+:51]([CH2:60][CH2:61][CH2:62][CH3:63])(CCCC)CCCC)CCC.[CH2:64]1[CH2:68][O:67][CH2:66][CH2:65]1>C(OCC)(=O)C>[CH3:39][O:41][C:65]1[CH:64]=[C:61]([CH:62]=[CH:63][C:66]=1[O:67][CH3:68])[CH2:60][NH:51][C@@H:9]([CH2:8][C@@H:7]([OH:6])[CH2:32][C:33](=[O:36])[NH:34][CH3:35])[CH2:10][CH2:11][C@@H:12]1[C@@H:21]2[C:16](=[CH:17][C@H:18]([CH3:29])[CH2:19][C@@H:20]2[O:22][C:23](=[O:28])[C@@H:24]([CH3:27])[CH2:25][CH3:26])[CH:15]=[CH:14][C@@H:13]1[CH3:30].[OH:6][CH:7]([CH2:32][C:33](=[O:36])[NH:34][CH3:35])[CH2:8][C:9](=[O:31])[CH2:10][CH2:11][CH:12]1[CH:21]2[C:16](=[CH:17][CH:18]([CH3:29])[CH2:19][CH:20]2[O:22][C:23](=[O:28])[CH:24]([CH3:27])[CH2:25][CH3:26])[CH:15]=[CH:14][CH:13]1[CH3:30]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 69856723HCID 69856723, compound

Product 2

HCID 69855632HCID 69855632, compoundHCID 86584759HCID 86584759, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 900 mg (1.65 mmol) of 2-methyl-butyric acid 8-[5-(tert.-butyl-dimethyl-silanyloxy)-6-methylcarbamoyl-3oxo-hexyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester in 5 ml of THF are added 700 mg (11.7 mmol) of acetic acid and 1.0 g (3.2 mmol) of tetrabutylammonium fluoride trihydrate. The reaction mixture is stirred for 3 hours at rt. It is then diluted with 30 ml of ethyl acetate and washed successively with a saturated aqueous sodium bicarbonate solution and water. The organic phase is dried over sodium sulfate and the solvent evaporated. The residue is crystallized from diethyl ether to afford the desired product 2-methyl-butyric acid 8-(5-hydroxy-6-methylcarbamoyl-3-oxo-hexyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester as white crystals.

Workup

  1. washwashed successively with a saturated aqueous sodium bicarbonate solution and water
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe solvent evaporated
  4. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-bb2c598558e34a6c9cdda8898f0bdc77
Source dataset
uspto-grants-2004_11
Patent number
US06818638B2

Reaction notes

Loading…