1-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea → 3-[3-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid

HRID 1979484Notes

Reaction equation

HRID 1979484 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:12][CH:11]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([O:38]CC3C=CC=CC=3)=[O:37])[CH:31]=2)=[O:28])[C:10]1=[O:46])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([O:5][C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:12][CH:11]([NH:26][C:27](=[O:28])[NH:29][C:30]2[CH:31]=[C:32]([CH:33]=[CH:34][CH:35]=2)[C:36]([OH:38])=[O:37])[C:10]1=[O:46])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 212017101-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

Product 1

HCID 212019863-[3-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acidYield 54.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5% Palladium carbon (300 mg) was added to a solution of 1-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea (960 mg) in ethanol (50 ml), the mixture was stirred at room temperature for 3 hours under hydrogen atmosphere. The reaction mixture was filtrated through a pad of Celite, and the filtrate was concentrated under reduced pressure. Isopropyl alcohol was added to the residue for crystallization, collected by filtrated, to thereby obtain 450 mg of the titled compound.

Workup

  1. filtrationThe reaction mixture was filtrated through a pad of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionIsopropyl alcohol was added to the residue for crystallization
  4. customcollected
  5. filtrationby filtrated

Sources & evidence

ORD record
ord-339ac69fe1fd44d8bdab808f71187d1e
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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