Hydrochloric Acid → (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

HRID 2222670Notes

Reaction equation

HRID 2222670 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10](=[O:45])[CH2:11][C@H:12]([O:37][Si](C(C)(C)C)(C)C)[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.Cl.C1([C@@H](NC(=O)C[C@H](O)CC(=O)/C=C/C2C(C3CC3)=NC3C(C=2C2C=CC(F)=CC=2)=CC=CC=3)C)C=CC=CC=1>C(O)C>[C:1]1([C@@H:7]([NH:9][C:10](=[O:45])[CH2:11][C@H:12]([OH:37])[CH2:13][C:14](=[O:36])/[CH:15]=[CH:16]/[C:17]2[N:18]([CH:33]([CH3:34])[CH3:35])[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:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11214592(E)-(R)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amideHCID 59712851(E)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-7-[3-(4-fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-5-oxo-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

can be prepared from (E)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-7-[3-(4-fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-5-oxo-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide by deprotection with HCl in ethanol according to the procedure described above for the preparation of (E)-(R)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide. Chromatography on silicagel with ethyl acetate/n-hexanes (9:1) as eluent affords (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 as a yellow foam. Rf=0.30 (TLC on silicagel, ethyl acetate/hexanes 9:1 as eluent). [α]D20=−35.5° (CH3OH, c=1) MS (ES+, m/z): 535 ([MNa]+, 100%); IR (KBr): 3307 (broad), 3061, 2973, 2932, 1645, 1590, 1539, 1495, 1452, 1421, 1371, 1339, 1273, 1221, 1155, 1138, 1105, 1095, 1048, 1016, 973, 910, 839, 815, 744, 719, 700 cm−1. Microanalysis: calculated (found) for C32H33FN2O3: 74.98 (74.20) % C, 6.49 (6.49) % H, 5.46 (5.49) % N, 3.71 (3.58) % F.

Sources & evidence

ORD record
ord-5ad939488d344a66aec70741abed9eb1
Source dataset
uspto-grants-2008_05
Patent number
US07371865B2

Reaction notes

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