Trityl chloride → HCID 21701358, compound

HRID 1596371Notes

Reaction equation

HRID 1596371 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=2[N:12]([CH2:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])=[O:22])[C:11](=[O:30])[CH:10]([NH:31][C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]3[NH:45][N:44]=[N:43][N:42]=3)[CH:36]=2)=[O:33])[N:9]=1.C(N(CC)CC)C.Cl[C:54]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=2[N:12]([CH2:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])=[O:22])[C:11](=[O:30])[CH:10]([NH:31][C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]3[N:45]([C:54]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)([C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)[C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)[N:44]=[N:43][N:42]=3)[CH:36]=2)=[O:33])[N:9]=1

Participants

8

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178423607HCID 178423607, compound

Product 1

HCID 21701358HCID 21701358, compoundYield 88.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(2-hydroxyphenacyl)-9-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-[3-(tetrazol-5-yl)phenyl]urea (150 mg), triethylamine (75 mg) and chlorotriphenylmethane (69 mg) in a mixture of N,N-dimethylformamide and tetrahydrofuran (1:3, 4 ml) was stirred overnight. Ethyl acetate and a saturated aqueous solution of sodium bicarbonate were added to the reaction mixture. The separated organic layer was washed with water and brine, and then dried over sodium sulfate. The solvent was evaporated in vacuo to afford an amorphous mass, which was triturated in diisopropyl ether and collected by filtration to afford N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(2-hydroxyphenacyl)-9-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-{3-[1-(triphenylmethyl)tetrazol-5-yl]phenyl}urea (186.0 mg, 88.6% yield) as a crystalline powder.

Workup

  1. washThe separated organic layer was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customto afford an amorphous mass, which
  5. customwas triturated in diisopropyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9fe016bb32874adbb32583699184be6f
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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