Acetic Acid → HCID 86761361, compound

HRID 1014978Notes

Reaction equation

HRID 1014978 reaction equation
[Si]([O:8][C@@H:9]1[C@@:38]2([CH3:39])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:40])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@@H:21]([O:23][CH:24]([C:27]([O:29][CH:30]([CH3:33])[CH2:31][CH3:32])=[O:28])[CH2:25][CH3:26])[CH3:22])[CH2:12][C@@H:11]([O:41][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>C(OCC)(=O)C>[OH:8][C@@H:9]1[C@@:38]2([CH3:39])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:40])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@@H:21]([O:23][CH:24]([C:27]([O:29][CH:30]([CH3:33])[CH2:31][CH3:32])=[O:28])[CH2:25][CH3:26])[CH3:22])[CH2:12][C@@H:11]([OH:41])[CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86761362HCID 86761362, compound

Product 1

HCID 86761361HCID 86761361, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

The mixture containing 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(1-ethyl-1-methylpropoxycarbonylmethoxy)pregna-5,7-diene from Example 23(2) (5.59 g), a 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride (79.5 ml, 79.5 ml) and acetic acid (2 ml) were mixed and stirred at an external temperature of 65° C. for 17 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed sequentially with aqueous potassium bisulfate, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After evaporation under reduced pressure to remove the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate:ethanol=5:5:0.3) to give the titled compound (2.43 g, 57% for 2 steps) as a pale yellow foam.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed sequentially with aqueous potassium bisulfate, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter evaporation under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate:ethanol=5:5:0.3)

Sources & evidence

ORD record
ord-e8a7d1cd02524fb29f14cbceaa1d9801
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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