4-t-Butoxycarbonylamino-N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-[N-(triphenylmethyl)tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-1-benzazepin-3-yl]-butanamide → HCID 178453476, compound

HRID 1591431Notes

Reaction equation

HRID 1591431 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][CH:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[N:17]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[N:43](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:42]=[N:41][N:40]=3)=[CH:29][CH:28]=2)[C:16]1=[O:63])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][CH:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[N:17]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[NH:43][N:42]=[N:41][N:40]=3)=[CH:31][CH:32]=2)[C:16]1=[O:63])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 190255074-t-Butoxycarbonylamino-N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-[N-(triphenylmethyl)tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-1-benzazepin-3-yl]-butanamide

Product 1

HCID 178453476HCID 178453476, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The intermediate obtained in Step B (349 mg, 0.40 mmol) was dissolved in 5 mL of methanol and hydrogenated at room temperature and one atmosphere over 70 mg of 20% Pd(OH)2 /C for 16 hours. The reaction mixture was filtered through Celite and solvent removed under vacuum. The crude product was purified by flash chromatography on silica, eluting with 10% methanol/ethyl acetate to afford 168 mg (0.28 mmol, 71%) of product. 1H NMR (200 MHz, CD3OD): 1.41 (s,9H), 1.72 (m,2H), 2.0-2.6 (m,6H), 3.24 (t,7 Hz,2H), 4.32 (m,1H), 4.85 (d,14 Hz,1H), 5.20 (d,14 Hz,1H), 6.9-7.7 (m,12H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite and solvent
  2. customremoved under vacuum
  3. customThe crude product was purified by flash chromatography on silica
  4. washeluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-4b95ce941ece4cc1adef8de645b56cf4
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

Loading…