Methanol → HCID 69691236, compound

HRID 1937177Notes

Reaction equation

HRID 1937177 reaction equation
Cl.Cl.[N:3]1([CH2:8][CH2:9][O:10][C:11]2[CH:40]=[CH:39][C:14]([CH2:15][C:16]3[C:17]4[CH:38]=[CH:37][CH:36]=[CH:35][C:18]=4[S:19][C:20]=3[C:21]3[CH:26]=[CH:25][C:24]([NH:27]C(C4N=CNC=4)=O)=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.[O:41]=[C:42]1[NH:46][CH:45]([C:47]([OH:49])=[O:48])[CH2:44][S:43]1.[CH3:50][OH:51].[NH4+].[OH-:53]>C(Cl)(Cl)Cl>[C:47]([OH:49])(=[O:48])[C:50]([OH:53])=[O:51].[N:3]1([CH2:8][CH2:9][O:10][C:11]2[CH:40]=[CH:39][C:14]([CH2:15][C:16]3[C:17]4[CH:38]=[CH:37][CH:36]=[CH:35][C:18]=4[S:19][C:20]=3[C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:47]([C@@H:45]4[CH2:44][S:43][C:42](=[O:41])[NH:46]4)=[O:49])=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 652722-Oxo-1,3-thiazolidine-4-carboxylic acidHCID 178478890HCID 178478890, compound

Product 1

HCID 69691236HCID 69691236, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

By essentially following the conditions described in Example l, Part F, the free base of the title compound was prepared as a foam from 2-(4-aminophenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene (Example 16; Part D) and (−)-2-oxo-4-thiazolidinecarboxylic acid in 67% yield following radial chromatography (SiO2; 1% then 2% then 4% MeOH in CHCl3 sat'd with NH4OH). The product was converted to the oxalate salt according to the proceedure described in Example 1, Part G.

Sources & evidence

ORD record
ord-7ee6735a75244ee482c610085ddcb713
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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