Acetic Acid → HCID 14206207, compound

HRID 329506Notes

Reaction equation

HRID 329506 reaction equation
CS(O[C@@H:6]([C@H:28]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:29][CH2:30][CH2:31][OH:32])[CH2:7][O:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)=O.CC(C)([O-])C.[K+].C(O)(=O)C>C(O)(C)(C)C>[CH2:34]([O:33][C@@H:28]1[CH2:29][CH2:30][CH2:31][O:32][C@H:6]1[CH2:7][O:8][C:9]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14206223HCID 14206223, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14206207HCID 14206207, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 26.08 g of (2R, 3R)-3-benzyloxy-6-hydroxy-1-triphenylmethoxy-2-hexyl methanesulfonate (prepared as described in Preparation 21) dissolved in 290 ml of t-butanol was added dropwise to a solution of 7.01 g of potassium t-butoxide in 250 ml of t-butanol, whilst maintaining the temperaure at 25° C. The mixture was then stirred at 40° C. for 4 hours. At the end of this time, 0.56 ml of acetic acid were added to the mixture, and the solvent was removed by distillation under reduced pressure. The residue was diluted with water, and then extracted three times with ethyl acetate. The combined extracts were washed with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was then subjected to column chromatography through 430 g of silica gel. 21.04 g of the title compound were obtained from those fractions eluted with a 95:5 by volume mixture of hexane and ethyl acetate, as crystals melting at 86.0°-88.0° C. (after recrystallization from methanol).

Workup

  1. customthe solvent was removed by distillation under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined extracts were washed with a saturated aqueous solution of sodium bicarbonate and with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-a7996db9268b4af5939d6e56e69eb516
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

Loading…