Methyl L-threoninate hydrochloride → HCID 178501563, compound

HRID 566280Notes

Reaction equation

HRID 566280 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10](SC)[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1.Cl.[CH3:23][O:24][C:25](=[O:31])[C@H:26]([C@@H:28]([CH3:30])[OH:29])[NH2:27]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:27][CH:26]([CH:28]([OH:29])[CH3:30])[C:25]([O:24][CH3:23])=[O:31])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 2734893Methyl L-threoninate hydrochlorideHCID 154992837-chloro-5-(2-fluorophenyl)-2-methylthio-3H-1,4-benzodiazepine

Product 1

HCID 178501563HCID 178501563, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 22.0 g of 7-chloro-5-(2-fluorophenyl)-2-methylthio-3H-1,4-benzodiazepine and 20.0 g of L-threonine methyl ester hydrochloride in 200 ml of pyridine was stirred at 75° C. for 5 h. The solvent was removed in a vacuum and the residue was purified by chromatography on 800 g of silica gel with dichloromethane containing 5% methanol. There were obtained 16.3 g (59%) of methyl 2-[7-chloro-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2-ylamino]-3-hydroxy-butyrate as a diastereomer mixture which was used without further purification as the starting product for the step described below.

Workup

  1. customThe solvent was removed in a vacuum
  2. customthe residue was purified by chromatography on 800 g of silica gel with dichloromethane containing 5% methanol

Sources & evidence

ORD record
ord-7cccf36d3c6b4997a9c57e148ffa3e6e
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

Loading…