3-Butenoic acid, ion(1-) → (3R,5S) t-butyl 6-acetoxy-3,5-dihydroxyhexanoate

HRID 2220022Notes

Reaction equation

HRID 2220022 reaction equation
[OH:1][C@H:2]([CH2:11][C@H:12]([OH:15])[CH2:13][OH:14])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C([CH2:18][C:19]([O-])=[O:20])=C>O1CCCC1>[C:19]([O:14][CH2:13][C@@H:12]([OH:15])[CH2:11][C@@H:2]([OH:1])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5])(=[O:20])[CH3:18]

Participants

4

Reactant 2

HCID 69710893-Butenoic acid, ion(1-)HCID 11148719Pitavastatin Impurity 75

Product 1

HCID 11402767(3R,5S) t-butyl 6-acetoxy-3,5-dihydroxyhexanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred 11 round bottom flask 700 ml tetrahydrofuran and 70.7 g (0.32 mol) of (3R,5S) t-butyl 3,5,6-trihydroxyhexanoate, 41 ml (0.46 mol) vinylacetate and 6.3 g of the supported lipase Chirazyme L2™ were charged. After 3 hours stirring at ambient temperature the lipase was removed by screening and the volatiles removed by distillation under vacuum. The mass of crude oil was 78.7 g and the major component was determined to be (3R,5S) t-butyl 6-acetoxy-3,5-dihydroxyhexanoate. This material was used directly in the next stage.

Workup

  1. additionwere charged
  2. customwas removed by screening
  3. customthe volatiles removed by distillation under vacuum

Sources & evidence

ORD record
ord-a2d7213013b94e08a7f0ada242b5d687
Source dataset
uspto-grants-2008_08
Patent number
US07416865B2

Reaction notes

Loading…