1-[1-(2-toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-tert-butoxycarbonylphenyl)urea → 3-[3-[1-(2-toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]ureido]benzoic acid

HRID 1979457Notes

Reaction equation

HRID 1979457 reaction equation
[C:1]1([CH3:47])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22](=[O:28])[C:23]3[S:27][CH:26]=[CH:25][CH:24]=3)[CH2:13][CH:12]([NH:29][C:30]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([O:41]C(C)(C)C)=[O:40])[CH:34]=3)=[O:31])[C:11]2=[O:46])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1>FC(F)(F)C(O)=O>[C:1]1([CH3:47])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22](=[O:28])[C:23]3[S:27][CH:26]=[CH:25][CH:24]=3)[CH2:13][CH:12]([NH:29][C:30](=[O:31])[NH:32][C:33]3[CH:34]=[C:35]([CH:36]=[CH:37][CH:38]=3)[C:39]([OH:41])=[O:40])[C:11]2=[O:46])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 212016271-[1-(2-toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-tert-butoxycarbonylphenyl)urea

Product 1

HCID 212017143-[3-[1-(2-toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]ureido]benzoic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-[1-(2-Toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-tert-butoxycarbonylphenyl)urea (3.35 g) was dissolved in trifluoroacetic acid (30 ml), and then stirred for one hour at room temperature. The reaction mixture was concentrated under reduced pressure, hexane was added to the residue for trituration, and collected by filtration, to thereby obtain 3.04 g of the title compound as colorless powder (Yield: 99%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, hexane
  2. additionwas added to the residue for trituration
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2020197cf4214ca388dda8c3845395b0
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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