Methanol → rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid 4-carboxy-phenyl ester

HRID 2065430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065430
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([N:14]2[CH2:18][CH:17]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:16]3([C:31]4[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:33])[CH:15]2[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[F:41])=[O:13])=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].CO>O1CCCC1.O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([N:14]2[CH2:18][CH:17]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:16]3([C:31]4[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:33])[CH:15]2[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[F:41])=[O:13])=[CH:7][CH:6]=1)([OH:4])=[O:2]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67337314rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid 4-methoxycarbonyl-phenyl ester

Produkt 1

HCID 67337713rac-(2'S,3'S,4'S)-6-chloro-2'-(3-chloro-2-fluoro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid 4-carboxy-phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a manner similar to the method described in Example 13, rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carboxylic acid 4-methoxycarbonyl-phenyl ester (10 mg, 0.02 mmol) was heated with aqueous LiOH (4 mg, 0.2 mmol) in tetrahydrofuran (3 mL), water (3 mL), and methanol (1 mL) at room temperature for 18 h to give rac-(2′S,3′S,4′S)-6-chloro-2′-(3-chloro-2-fluoro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carboxylic acid 4-carboxy-phenyl ester as a white solid (Yield, 8 mg, 82%).

Aufarbeitung

  1. customto give

Quellen und Nachweise

ORD-Eintrag
ord-9f95590469ae44e29c54a2fc2a87a1f6
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288431B2

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