Trifluoroacetic acid → 3-[3-(1-cyclohexylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid

HRID 1979475Notes

Reaction equation

HRID 1979475 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([C:14]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:20][CH:19]([NH:34][C:35]([NH:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([O:46]C(C)(C)C)=[O:45])[CH:39]=3)=[O:36])[C:18]2=[O:51])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C(Cl)Cl>[CH:8]1([C:14]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)[CH2:20][CH:19]([NH:34][C:35](=[O:36])[NH:37][C:38]3[CH:39]=[C:40]([CH:41]=[CH:42][CH:43]=3)[C:44]([OH:46])=[O:45])[C:18]2=[O:51])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 212018681-(1-cyclohexylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea

Product 1

HCID 212020303-[3-(1-cyclohexylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acidYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to a solution of 1-(1-cyclohexylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea (560 mg) in methylene chloride (5 ml), the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, etanol was added to the residue for crystallization, collected by filtration, to thereby obtain 330 mg of the title compound.

Workup

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

Sources & evidence

ORD record
ord-0d1fb44c144d4fbdbe8b88f0770484d9
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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