Hydrochloric Acid → 5-(4-fluorophenyl)-beta,delta-dihydroxy-2-(1-methylethyl)-N,N,4-triphenyl-3-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanamide
Reaction equation
[C:1]1([N:7]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:8](=[O:50])[CH2:9][C@@H:10]2[O:15]C(C)(C)[O:13][C@H:12]([CH2:18][CH2:19][N:20]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[C:23]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:22]([C:38]([NH:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:39])=[C:21]3[CH:47]([CH3:49])[CH3:48])[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>CO>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]2[N:20]([CH2:19][CH2:18][CH:12]([OH:13])[CH2:11][CH:10]([OH:15])[CH2:9][C:8]([N:7]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:50])[C:21]([CH:47]([CH3:49])[CH3:48])=[C:22]([C:38]([NH:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:39])[C:23]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:27]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
U.S. Pat. No. 5,298,627 discloses that (4R-cis)-1-[2-[6-[2-(diphenylamino)-2-oxoethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide is dissolved in methanol and reacted with hydrochloric acid to form [R—(R*,R*)]-5-(4-fluorophenyl)-β,δ-dihydroxy-2-(1-methylethyl)-N,N,4-triphenyl-3-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanamide, which is mixed with methanol and sodium hydroxide. The filtrate is washed with tert-butyl methyl ester and the aqueous layer is acidified by using hydrochloric acid, then extracted with tert-butyl methyl ester to afford the sodium salt of [R—(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid.
Sources & evidence
- ORD record
- ord-9dadc13fb3fb47b69e9520f3e6cae171
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497370B2
Reaction notes
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