(S)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-phosphonooxy-propyl ester → (S)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-phosphonooxy-ethyl ester

HRID 585157Notes

Reaction equation

C([O:5][P:6]([O:38]C(C)(C)C)([O:8][CH2:9][CH2:10][O:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=2)[C@@:16]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])([F:27])[C:15]1=[O:37])=[O:13])=[O:7])(C)(C)C.P(OC(C)COC(N1C2C(=CC=C(C(F)(F)F)C=2)[C@@](C2C=C(Cl)C=CC=2OC)(F)C1=O)=O)(O)(O)=O>>[P:6]([O:8][CH2:9][CH2:10][O:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([F:24])([F:25])[F:26])[CH:21]=2)[C@@:16]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])([F:27])[C:15]1=[O:37])=[O:13])([OH:7])([OH:38])=[O:5]

Participants

Reactant 2

HCID 10196400(S)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-phosphonooxy-propyl ester

HCID 69329460(S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-(di-tert-butoxy-phosphoryloxy)-ethyl ester

Product 1

HCID 10289471(S)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-phosphonooxy-ethyl ester

Procedure

Using (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-(di-tert-butoxy-phosphoryloxy)-ethyl ester ((S)-VII, n=1) as starting material, the title compound was prepared analogously to (S)-3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-phosphonooxy-propyl ester; (S)-Ib, n=2) in 83%. 1H NMR (CDCl3, 500 MHz) δ 8.23 (s, 1H), 7.73 (d, 1H), 7.45 (d, 1H), 7.30 (d, 1H), 7.28 (d, 1H), 6.75 (d, 1H), 4.59 (m, 2H), 4.33 (m, 2H), 3.51 (s, 3H); MS (m/e) 525.95 (M+−1); 31P NMR (CDCl3, 500 MHz) δ 1.87; 19F NMR (CDCl3, 500 MHz) δ−63.25, 153.8; Anal. Calcd. for C19H15ClF4NO8P·0.159H2O: C=41.60%, H=3.18%, N=2.55%; Found: C=41.57%, H=2.92%, N=2.51%.

Sources & evidence

ORD record: ord-1a1f3a9025eb4a9eba7c3186f636c710
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930100B2

Reaction notes

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