Sodium Chloride → HCID 57590164, compound

HRID 1784039Notes

Reaction equation

HRID 1784039 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@@H:7]1[C:12]([O:14]CC)=[O:13])=[O:5])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Na+].[Cl-].[OH-].[Na+]>>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@@H:7]1[C:12]([OH:14])=[O:13])=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 11862697HCID 11862697, compound

Product 1

HCID 57590164HCID 57590164, compoundYield 86%

Procedure

An emulsion of 1.7 g 41a in an aqueous buffer (potassium phosphate 3 mM, NaCl 0.1 M) was adjusted to pH 7.5. Under stirring at room temperature the hydrolysis was performed with 15 mg lipase OF from Candida rugosa under pH control (pH-static, 1M NaOH). After consumption of 6.5 ml 1M NaOH solution and 7 h the reaction mixture was washed with 50 ml t-butyl methyl ether. The aqueous layer was adjusted to pH 2.0 (conc. HCl) and was extracted with 85 ml ethyl acetate. Drying over sodium sulfate, evaporation and drying overnight on a high vacuum yielded 1.28 g of the title compound 41b. MS: 197.2 (M−H)−; chiral GC: ee 99.4%.

Workup

  1. customAfter consumption of 6.5 ml 1M NaOH solution and 7 h the reaction mixture
  2. washwas washed with 50 ml t-butyl methyl ether
  3. extractionwas extracted with 85 ml ethyl acetate
  4. dry with materialDrying over sodium sulfate, evaporation
  5. customdrying overnight on a high vacuum

Sources & evidence

ORD record
ord-34aaaf9b7bff4c39818c9297ecafd186
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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