HCID 86600608, compound → HCID 58787677, compound

HRID 1375728Notes

Reaction equation

HRID 1375728 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:41][CH3:42])=[C:6]([C@@:8]2([F:40])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([C:21]([O:23][CH2:24][C:25]([O:27]CC(OCC3C=CC=CC=3)=O)=[O:26])=[O:22])[C:9]2=[O:39])[CH:7]=1>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:41][CH3:42])=[C:6]([C@@:8]2([F:40])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:19])([F:18])[F:20])=[CH:14][CH:15]=3)[N:10]([C:21]([O:23][CH2:24][C:25]([OH:27])=[O:26])=[O:22])[C:9]2=[O:39])[CH:7]=1

Participants

4

Reactant 1

HCID 86600608HCID 86600608, compound

Product 1

HCID 58787677HCID 58787677, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-2-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carbonyloxy)acetic acid, benzyloxycarbonylmethyl ester (XII2) (95 mg, 0.17 mmol) in methanol (50 mL) was hydrogenated with Pd—C(10%) as catalyst at room temperature. Prep. HPLC purification afforded the title compound (42.4 mg) with 98% HPLC purity (yield 53.3%). 1H NMR (CDCl3, 500 MHz) δ 8.34 (s, 1H), 7.79 (d, 1H), 7.47 (d, 1H), 7.36 (dd, 1H), 7.31 (dd, 1H), 6.76 (dd, 1H), 5.08 (d, 1H), 4.96 (d, 1H), 3.57 (s, 3H); LC-MS, 462.88 (MH+, 99%); MS (m/e) 462 (M+1).

Workup

  1. customHPLC purification

Sources & evidence

ORD record
ord-e6b6eda5773448c3a894a779ad54e86b
Source dataset
uspto-grants-2007_01
Patent number
US07169803B2

Reaction notes

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