Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether → HCID 53996491, compound

HRID 2396236Notes

Reaction equation

HRID 2396236 reaction equation
[CH2:1]([C:3]([O:9][CH3:10])([CH2:7][CH3:8])[C:4]([OH:6])=[O:5])[CH3:2].[Si:11]([O:18][C@H:19]1[CH2:28][C@H:27](O)[C@H:26]2[C:21]([CH:22]=[CH:23][C@H:24]([CH3:47])[C@@H:25]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:33]2)=[CH:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]>>[Si:11]([O:18][C@H:19]1[CH2:28][C@H:27]([O:5][C:4](=[O:6])[C:3]([CH2:7][CH3:8])([O:9][CH3:10])[CH2:1][CH3:2])[C@H:26]2[C:21]([CH:22]=[CH:23][C@H:24]([CH3:47])[C@@H:25]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:41])[CH3:42])[CH2:33]2)=[CH:20]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) EtherHCID 18988632HCID 18988632, compound

Product 1

HCID 53996491HCID 53996491, compoundYield 45.3%

Procedure

A procedure similar to that described in Example 10, above, was followed, but using 1.28 g of 2-ethyl-2-methoxybutyric acid and 1.0 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-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above], to give 558 mg of the title compound as a colorless foam.

Sources & evidence

ORD record
ord-4f538bc9e60c4c8c988960fe06773734
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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