Trifluoroacetic acid → HCID 54152628, compound

HRID 258101Notes

Reaction equation

HRID 258101 reaction equation
C(OC([NH:8][C@H:9]([C:44]([O:46]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:45])[CH2:10][S:11][CH2:12][CH2:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:17][C@@H:16]([NH:31][C:32]([C:34]2[NH:35][C:36]3[C:41]([CH:42]=2)=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[C:15]1=[O:43])=O)(C)(C)C.C(OC(N[C@H](C(OC(C1C=CC=CC=1)C1C=CC=CC=1)=O)CSCCN1C2C=CC=CC=2C(C2C=CC=CC=2)=N[C@H](NC(C2NC3C(C=2)=CC=CC=3)=O)C1=O)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C@H:9]([C:44]([OH:46])=[O:45])[CH2:10][S:11][CH2:12][CH2:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:17][C@@H:16]([NH:31][C:32]([C:34]2[NH:35][C:36]3[C:41]([CH:42]=2)=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[C:15]1=[O:43]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 54503167HCID 54503167, compoundHCID 56985990HCID 56985990, compound

Product 1

HCID 54152628HCID 54152628, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of a mixture (0.66 g) of (3R)-1-[2-((2R)-2-tert-butoxycarbonylamino-2-benzhydryloxycarbonylethylthio)ethyl]-1, 3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-2H-1,4-benzodiazepine-2-one and (3S)-1-[2-((2R)-2-tert-butoxycarbonylamino-2-benzhydryloxycarbonylethylthio)ethyl]-1, 3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-2H-1,4-benzodiazepine-2-one, anisole (0.6 ml), trifluoroacetic acid (1.5 ml) and dichloromethane (15 ml) was stirred for 3.0 hours at room temperature. After removal of the solvent, the residue was mixed with ethyl acetate (50 ml) and water (50 ml). The mixture was adjusted to pH 6-7 with 5% aqueous solution of sodium bicarbonate under stirring. The organic layer was separated and concentrated. The resultant precipitate was collected by filtration, washed with water and dried to give a mixture (0.20 g) of (3R)-1-[2-((2R)-2-amino-2-carboxyethylthio)ethyl]-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-2H-1,4-benzodiazepine-2-one and (3S)-1-[2-((2R)-2-amino-2-carboxyethylthio)ethyl]-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-2H-1,4-benzodiazepine-2-one.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was mixed with ethyl acetate (50 ml) and water (50 ml)
  3. stirringunder stirring
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. filtrationThe resultant precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-ed2af429e87b479fb0208704bf2b424b
Source dataset
uspto-grants-1993_11
Patent number
US05264433

Reaction notes

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