L-Valine → 2-[2-[2-(1-Carboxy-2-methylpropylcarbamoyl) phenyldisulfanyl]benzoylamino]-3-methylbutanoic acid

HRID 53672

Reaction equation

HRID 53672 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[C:9](Cl)(=[O:27])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>>[C:6]([CH:2]([NH:1][C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][CH:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])=[O:21])=[O:27])[CH:3]([CH3:5])[CH3:4])([OH:8])=[O:7]

Participants

3

Reactant 2

HCID 6287L-ValineHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 4653642-[2-[2-(1-Carboxy-2-methylpropylcarbamoyl) phenyldisulfanyl]benzoylamino]-3-methylbutanoic acid

Procedure

Using the method employed in Preparation 30, 17.8 g (0.15 mol) of D,L valine was reacted with 17.2 g (0.05 mol) of 2,2'-dithiobisbenzoyl chloride to produce 11.4 g of the title compound after recrystallization from acetic acid, mp 226.5°-227.5° C.

Sources & evidence

ORD record
ord-6384edd1f37f4d659d1d749143aaebcc
Source dataset
uspto-grants-1997_04
Patent number
US05620997

Linked notes

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