Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether → HCID 54300129, compound

HRID 2396242Notes

Reaction equation

HRID 2396242 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])=[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:10][C:9](=[O:11])[C:8]([O:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:15][CH:14]=2)([CH3:13])[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 18988391HCID 18988391, compound

Product 1

HCID 54300129HCID 54300129, compound

Procedure

A procedure similar to that described in Example 10, above, was followed, but using 770 mg of 2-(4-fluorobenzyloxy)-2-methylpropionic acid and 1.0 gof (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 1.17 g of the title compound as a colorless foam.

Sources & evidence

ORD record
ord-a5aac57882874b68a125196aa4233036
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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