Dichloromethane → HCID 58017136, compound

HRID 883667Notes

Reaction equation

HRID 883667 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[C:8]([CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]1=[O:29])=[O:5])[CH3:2].ClCCl>>[Cl:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7](=[O:29])[C:8]2([CH2:21][C:22]([OH:24])=[O:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 58017142HCID 58017142, compound

Product 1

HCID 58017136HCID 58017136, compoundYield 99%

Procedure

To a solution of diethyl-3-(2-tert-butoxy-2-oxoethyl)-5-chloro-2-oxoindoline-1,3-dicarboxylate, intermediate 51, (1.83 g, 4.30 mmol) in dichloromethane (30 ml) trifluoroacetic acid (3.18 ml, 42.97 mmol) was added at 0-5° C. Stirring was continued at 0-5° C. for 30 minutes and at ambient temperature overnight. Evaporation and drying under high vacuum gave the title compound (1.57 g, 99%) as colorless oil (HPLC purity: 85%). MS (ESI+): 370.2

Workup

  1. customEvaporation
  2. customdrying under high vacuum

Sources & evidence

ORD record
ord-886036f70a364dd2ad3875a5eb919e01
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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