Hydrochloric Acid → 5-(4-fluorophenyl)-beta,delta-dihydroxy-2-(1-methylethyl)-N,N,4-triphenyl-3-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanamide

HRID 1836701Notes

Reaction equation

HRID 1836701 reaction equation
Cl.[C:2]1([N:8]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:9](=[O:51])[CH2:10][C@@H:11]2[O:16]C(C)(C)[O:14][C@H:13]([CH2:19][CH2:20][N:21]3[C:25]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[C:24]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:23]([C:39]([NH:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:40])=[C:22]3[CH:48]([CH3:50])[CH3:49])[CH2:12]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:25]2[N:21]([CH2:20][CH2:19][CH:13]([OH:14])[CH2:12][CH:11]([OH:16])[CH2:10][C:9]([N:8]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:51])[C:22]([CH:48]([CH3:50])[CH3:49])=[C:23]([C:39]([NH:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:40])[C:24]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 111255291-(2-((4R,6R)-6-(2-(diphenylamino)-2-oxoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)ethyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide

Product 1

HCID 190063585-(4-fluorophenyl)-beta,delta-dihydroxy-2-(1-methylethyl)-N,N,4-triphenyl-3-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

U.S. Pat. No. 5,298,627, also discloses a process for making the hemicalcium salt. In Example 1 of this patent, (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 using aqueous hydrochloric acid and extracted with tert-butyl methyl ester to form 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. The sodium salt is converted to the hemicalcium salt by the addition of calcium acetate in water.

Sources & evidence

ORD record
ord-aef36a0b225243d1bef5bbb7018ea0b9
Source dataset
uspto-grants-2004_08
Patent number
US06777552B2

Reaction notes

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