DL-2-Phenoxypropionic acid → HCID 15341224, compound

HRID 2396218Notes

Reaction equation

HRID 2396218 reaction equation
[O:1]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:13]([O:20][C@H:21]1[CH2:30][C@H:29](O)[C@H:28]2[C:23]([CH:24]=[CH:25][C@H:26]([CH3:49])[C@@H:27]2[CH2:32][CH2:33][C@H:34]2[O:39][C:38](=[O:40])[CH2:37][C@H:36]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH2:35]2)=[CH:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>>[Si:13]([O:20][C@H:21]1[CH2:30][C@H:29]([O:10][C:9](=[O:11])[CH:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:12])[C@H:28]2[C:23]([CH:24]=[CH:25][C@H:26]([CH3:49])[C@@H:27]2[CH2:32][CH2:33][C@H:34]2[O:39][C:38](=[O:40])[CH2:37][C@H:36]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:43])[CH3:44])[CH2:35]2)=[CH:22]1)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 13658DL-2-Phenoxypropionic acidHCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether

Product 1

HCID 15341224HCID 15341224, compoundYield 74.4%

Procedure

A procedure similar to that described in Example 1, above, was followed, but using 598 mg of (2RS)-2-phenoxypropionic 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 944 mg of the title compound as a colorless foam.

Sources & evidence

ORD record
ord-54a7190a660340c9b0243abe96a89469
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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