Water → HCID 20097471, compound

HRID 258105Notes

Reaction equation

HRID 258105 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][C:19]3[NH:23][N:22]=[N:21][N:20]=3)[C:10](=[O:24])[CH:9]([N:25]3[C:29](=[O:30])[C:28]4=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]4[C:26]3=[O:35])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:36](Cl)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C.O>CN(C)C=O>[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][C:19]3[N:20]([C:36]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[N:21]=[N:22][N:23]=3)[C:10](=[O:24])[CH:9]([N:25]3[C:29](=[O:30])[C:28]4=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]4[C:26]3=[O:35])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178516700HCID 178516700, compound

Product 1

HCID 20097471HCID 20097471, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3RS)-1,3-dihydro-5-phenyl-3-phthalimido-1-[(1H-tetrazol-5-yl)methyl]-2 H-1,4-benzodiazepin-2-one (100 g) and trityl chloride (61.96 g) in N,N-dimethylformamide (1.8 l) was added dropwise triethylamine (36.1 ml) under stirring and cooling in an ice-bath. The mixture was stirred for 10 minutes at the same temperature and for 20 hours at ambient temperature. The reaction mixture was poured into water (18 l) under stirring and the resultant precipitate was collected by filtration, washed with water several times and dried in vacuo at 60° C. for 8 hours to give (3RS)-1,3-dihydro-5-phenyl-3-phthalimido-1-[(1 -trityl-1H-tetrazol-5-yl)-methyl]-2H-1,4-benzodiazepin-2-one (128.2 g).

Workup

  1. temperaturecooling in an ice-bath
  2. stirringThe mixture was stirred for 10 minutes at the same temperature and for 20 hours at ambient temperature
  3. stirringunder stirring
  4. filtrationthe resultant precipitate was collected by filtration
  5. washwashed with water several times
  6. customdried in vacuo at 60° C. for 8 hours

Sources & evidence

ORD record
ord-2e87f2b313f9441c99e874edb5c95602
Source dataset
uspto-grants-1993_11
Patent number
US05264433

Reaction notes

Loading…