Water → HCID 16667332, compound

HRID 852461Notes

Reaction equation

HRID 852461 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[I:13][C:14]1[CH:34]=[CH:33][CH:32]=[CH:31][C:15]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)=[O:17].C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[I:13][C:14]1[CH:34]=[CH:33][CH:32]=[CH:31][C:15]=1[C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:26][CH2:27][N:28]([CH:4]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:3]([O:2][CH3:1])=[O:12])[CH2:29][CH2:30]2)=[CH:23][CH:24]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 22499406HCID 22499406, compound

Product 1

HCID 16667332HCID 16667332, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

α-Bromo-benzeneacetic acid methyl ester (0.0123 mol) was added at room temperature to a mixture of intermediate (28) (0.0123 mol) and Na2CO3 (0.0123 mol) in DMF (50 ml). The mixture was stirred at room temperature for 2 hours. Water was added. The mixture was stirred at room temperature for 15 minutes. The precipitate was filtered, washed with diethyl ether and dried, yielding 5.8 g of 4-[4-[(2-iodobenzoyl)amino]phenyl]-α-phenyl-1-piperazine-acetic acid, methyl ester (intermediate 29).

Workup

  1. stirringThe mixture was stirred at room temperature for 15 minutes
  2. filtrationThe precipitate was filtered
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-c9e605c21c00425e80464a5aec96f98e
Source dataset
uspto-grants-2007_08
Patent number
US07253157B2

Reaction notes

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