Oxalic Acid → HCID 22994323, compound

HRID 1167964Notes

Reaction equation

HRID 1167964 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]([C:19]2[S:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[C:20]=2[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:31][CH:30]=2)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])([O:3][CH3:4])=[O:2].C(Cl)Cl.[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48]>CCOC(C)=O>[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48].[C:1]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]([C:19]2[S:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[C:20]=2[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]3[CH2:39][CH2:40][CH2:41][CH2:42]3)=[CH:31][CH:30]=2)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 6344DichloromethaneHCID 12087656HCID 12087656, compound

Product 1

HCID 22994323HCID 22994323, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in quantitative yield from methyl 2-(3-carbomethoxypropoxy)-5-[3-(4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]benzoate (Example 2, Part A) by treating a solution of the diester in 3:1 EtOAc:CH2Cl2 with an equimolar amount of 0.5 M oxalic acid in EtOAc. The resulting slurry was stirred at room temperature about 2 h before it was concentrated in vacuo to provide the title product as a solid.

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-43927d8e079f48548ff96981b5fdcc29
Source dataset
uspto-grants-2003_09
Patent number
US06620837B1

Reaction notes

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