Acetonitrile → sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate

HRID 2219832Notes

Reaction equation

[CH3:1][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[C@H:15]([OH:24])[CH2:16][C@H:17]([OH:23])[CH2:18][C:19]([O:21]C)=[O:20])=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:3].[OH-].[Na+:33].C(#N)C>O.C(O)CCC>[CH3:3][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[CH:15]([OH:24])[CH2:16][CH:17]([OH:23])[CH2:18][C:19]([O-:21])=[O:20])=[C:11]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2)[CH3:1].[Na+:33]

Participants

Conditions

Temperature: 80 °C

Procedure

Fluvastatin methyl ester (2.0 g) was added to a solution of NaOH (1 eq.) in water (0. 5 ml) and butan-1-ol (8 ml). The mixture was stirred at about 80° C. for 4 h, after which the starting material was not detected by HPLC. Then, acetonitrile (40 ml) was dripped into the solution and the mixture was cooled slowly to room temperature and stirred overnight. The product was isolated by filtration under nitrogen, washed with acetonitrile (15 ml) and dried at 50° C. in a vacuum oven for 24 h to obtain fluvastatin sodium Form VI (1.65 g, 81%).

Workup

temperaturethe mixture was cooled slowly to room temperature
stirringstirred overnight
customThe product was isolated by filtration under nitrogen
washwashed with acetonitrile (15 ml)
customdried at 50° C. in a vacuum oven for 24 h

Sources & evidence

ORD record: ord-0396209952614805abb2c4e86eb734fc
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414140B2

Reaction notes

Loading…