Acetate → HCID 131710090, compound

HRID 267616Notes

Reaction equation

HRID 267616 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([O:24][CH3:25])=[O:23])=[CH:3]1.C([O-])(=O)C>CC(C)=O>[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([O:24][CH3:25])=[O:23])=[CH:3]1

Participants

4

Reactant 2

HCID 175AcetateHCID 86733133HCID 86733133, compound

Product 1

HCID 131710090HCID 131710090, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This crude ester (about 600 mg.) was dissolved in acetone (50 ml.) and pH 5 acetate buffer was added. The solution was refluxed for 45 minutes, then concentrated by evaporation under reduced pressure, diluted with water and extracted with chloroform. The organic solution was dried over sodium sulphate and evaporated to an oil which was purified by preparative TLC and recrystallisation of the main band from acetone/petrol to give title compound (176 mg.) as off-white prisms, m.p. 121°-125°, [α]D + 215°.

Workup

  1. temperatureThe solution was refluxed for 45 minutes
  2. concentrationconcentrated by evaporation under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with chloroform
  5. dry with materialThe organic solution was dried over sodium sulphate
  6. customevaporated to an oil which
  7. customwas purified by preparative TLC and recrystallisation of the main band from acetone/petrol

Sources & evidence

ORD record
ord-b748dd4ef7f349f18d4def1cd36456d6
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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