(3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxy-N-((S)-1-phenylethyl)hept-6-enamide → (E)-(3R,5S)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide

HRID 2222671Notes

Reaction equation

HRID 2222671 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10](=[O:38])[CH2:11][C@H:12]([OH:37])[CH2:13][C:14](=[O:36])/[CH:15]=[CH:16]/[C:17]2[N:18]([CH:33]([CH3:35])[CH3:34])[C:19]3[C:24]([C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([C@@H](NC(=O)C[C@H](O)C[C@H](O)/C=C/C2C(C3CC3)=NC3C(C=2C2C=CC(F)=CC=2)=CC=CC=3)C)C=CC=CC=1>>[C:1]1([C@@H:7]([NH:9][C:10](=[O:38])[CH2:11][C@H:12]([OH:37])[CH2:13][C@H:14]([OH:36])/[CH:15]=[CH:16]/[C:17]2[N:18]([CH:33]([CH3:35])[CH3:34])[C:19]3[C:24]([C:25]=2[C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 11421120(3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxy-N-((S)-1-phenylethyl)hept-6-enamideHCID 59712858(E)-(R)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3-hydroxy-5-oxo-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide

Product 1

HCID 59712856(E)-(3R,5S)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide

Procedure

can be prepared from (E)-(R)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3-hydroxy-5-oxo-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide according to the procedures described above for the preparation of (E)-(3R,5S)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide. Chromatography on silicagel with ethyl acetate/hexanes (9:1) as eluent affords (E)-(3R,5S)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide as a light yellow foam. Rf=0.175 (TLC on silicagel, ethyl acetate/hexanes 9:1 as eluent). [α]D20 =−16.7° (CH3OH, c=1). MS (ES+, m/z): 537 ([M+Na]+, 100%); IR(KBr): 3310 (broad), 3049, 2974, 2934, 2875, 1644, 1604, 1545, 1501, 1457, 1420, 1371, 1346, 1219, 1155, 1104, 1065, 1045, 1018, 970, 944, 837, 814, 742, 718, 700, 565.

Sources & evidence

ORD record
ord-7760220179294b57981022eea34b6710
Source dataset
uspto-grants-2008_05
Patent number
US07371865B2

Reaction notes

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