Trifluoroacetic acid → Z-360

HRID 1979468Notes

Reaction equation

HRID 1979468 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]([CH2:14][N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:18][C@@H:17]([NH:32][C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([O:44]C(C)(C)C)=[O:43])[CH:37]=2)=[O:34])[C:16]1=[O:49])=[O:13])([CH3:11])([CH3:10])[CH3:9]>C(Cl)Cl>[C:8]([C:12]([CH2:14][N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:18][C@@H:17]([NH:32][C:33](=[O:34])[NH:35][C:36]2[CH:37]=[C:38]([CH:39]=[CH:40][CH:41]=2)[C:42]([OH:44])=[O:43])[C:16]1=[O:49])=[O:13])([CH3:11])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53986084(R)-(-)-1-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea

Product 1

HCID 9872609Z-360Yield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (40 ml) was added to a solution of (R)-(−)-1-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea (8 g) in methylene chloride (40 ml), the mixture was stirred for one hour at room temperature. The reaction mixture was concentrated under reduced pressure, a mixed solvent (32 ml) of diisopropyl ether and ethanol (15:1) was added to the residue for crystallization, collected by filtration, to thereby obtain 6.35 g of the title compound (Yield 88%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona mixed solvent (32 ml) of diisopropyl ether and ethanol (15:1) was added to the residue for crystallization
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-88e8f9fb27ab465e93452a5db4a01bff
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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