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

HRID 14360

Reaktionsgleichung

Reaktionsgleichung von HRID 14360
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. addition′ were charged
  2. customwas removed by screening
  3. customthe volatiles removed by distillation under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f2bfecf93598413ebb4cf2155f2a2ec6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732171B2

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