Hydrochloric Acid → (4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxylic acid

HRID 2057120Notes

Reaction equation

[CH2:1]([NH:8][C@H:9]([C@@H:13]1[CH2:17][S:16][C:15](=[O:18])[N:14]1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:10](=[O:12])N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH2:27]>CN(C)C=O>[CH2:19]([N:14]1[C@@H:13]([CH2:17][SH:16])[C@H:9]([C:10]([OH:12])=[O:27])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:15]1=[O:18])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 85 °C

Procedure

In 200 ml of N,N-dimethylformamide was dissolved 100 g of (4R)-4-[(1R)-1-(N-benzylamino)-1-carbamoylmethyl]-3-benzylthiazolidin-2-one, and under nitrogen atmosphere, the solution was stirred at 85° C. for 5 hours. At 90° C. to 95° C., 200 ml of 35% hydrochloric acid was added dropwise to the solution, and the mixture was stirred for 1 hour and 15 minutes. Moreover, 100 ml of 35% hydrochloric acid was added dropwise, and the mixture was stirred for 2 hours. Then, 200 ml of water was added dropwise to the mixture at 85° C. The solution was ice-cooled, and precipitated crystal was collected by filtration, washed with water and then dried at 50° C. for 17 hours to give 93.1 g of (4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)-imidazolidin-4-carboxylic acid as colorless crystal.

Workup

stirringthe mixture was stirred for 1 hour and 15 minutes
stirringthe mixture was stirred for 2 hours
temperaturecooled
customprecipitated crystal
filtrationwas collected by filtration
washwashed with water
customdried at 50° C. for 17 hours

Sources & evidence

ORD record: ord-fa84829124534523a9b2870cc2cef96a
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335778B2

Reaction notes

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