Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether → HCID 57234193, compound

HRID 2396173Notes

Reaction equation

HRID 2396173 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]([CH3:13])([CH2:11][CH3:12])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[Si:16]([O:23][C@H:24]1[CH2:33][C@H:32](O)[C@H:31]2[C:26]([CH:27]=[CH:28][C@H:29]([CH3:52])[C@@H:30]2[CH2:35][CH2:36][C@H:37]2[O:42][C:41](=[O:43])[CH2:40][C@H:39]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])[CH2:38]2)=[CH:25]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>>[Si:16]([O:23][C@H:24]1[CH2:33][C@H:32]([O:9][C:8](=[O:10])[C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([CH3:1])=[CH:3][CH:4]=2)([CH3:13])[CH2:11][CH3:12])[C@H:31]2[C:26]([CH:27]=[CH:28][C@H:29]([CH3:52])[C@@H:30]2[CH2:35][CH2:36][C@H:37]2[O:42][C:41](=[O:43])[CH2:40][C@H:39]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:46])[CH3:47])[CH2:38]2)=[CH:25]1)([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) EtherHCID 18988618HCID 18988618, compound

Product 1

HCID 57234193HCID 57234193, compoundYield 85%

Procedure

A procedure similar to that described in Example 10, above, was followed, but using 600 mg of (2RS)-2-(4-methylphenoxy)-2-methylbutyric acid and 1.32 g of (4R,6R)-6-{(1S,2S,6S,8S,8aR)-2-[1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-napthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above], to give 1.51 g of the title compound as a colorless foam.

Sources & evidence

ORD record
ord-6f6b2e013e714bf593119f44a1c2af1c
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

Loading…