Potassium Hydroxide → (1, 1-dimethyl-2-(4-oxo-5-(2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-ylmethyl)-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)-carbamic acid tert-butyl ester

HRID 398787Notes

Reaction equation

HRID 398787 reaction equation
[OH-].[K+].[C:3]([O:7][C:8](=[O:33])[NH:9][C:10]([CH3:32])([CH3:31])[CH2:11][C:12](=[O:30])[NH:13][CH:14]1[C:20](=[O:21])[NH:19][C:18]2[CH:22]=[CH:23][C:24]3[C:29]([C:17]=2[CH2:16][CH2:15]1)=[CH:28][CH:27]=[CH:26][CH:25]=3)([CH3:6])([CH3:5])[CH3:4].Br[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[C:48]2[N:52]([C:53]([C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[N:51]=[N:50][N:49]=2)=[CH:38][CH:37]=1.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C.O>[C:3]([O:7][C:8](=[O:33])[NH:9][C:10]([CH3:32])([CH3:31])[CH2:11][C:12](=[O:30])[NH:13][CH:14]1[C:20](=[O:21])[N:19]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:48]3[N:52]([C:53]([C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)([C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)[C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[N:51]=[N:50][N:49]=3)=[CH:40][CH:41]=2)[C:18]2[CH:22]=[CH:23][C:24]3[C:29]([C:17]=2[CH2:16][CH2:15]1)=[CH:28][CH:27]=[CH:26][CH:25]=3)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 53757316HCID 53757316, compound

Product 1

HCID 54197216(1, 1-dimethyl-2-(4-oxo-5-(2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-ylmethyl)-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)-carbamic acid tert-butyl esterYield 49.9%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of dry powdered potassium hydroxide (0.23 g, 4.0 mmol) and (1,1-dimethyl-2-(4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)carbamic acid tert-butyl ester (0.49 g, 1.0 mmol) in DMSO (15 ml) was stirred for 0.5 h under an atmosphere of nitrogen. 5-(4'-Bromomethyl-biphenyl-2-yl)-N-(triphenylmethyl)tetrazole (0.59 g, 1.1 mmol) was added and the mixture was stirred for 1 h. A 10% aqueous solution of ammoniumchloride (30 ml), water (100 ml) and ethyl acetate (60 ml) were added and the phases were separated. The organic layer was dried (MgSO4), and the solvent was evaporated in vacuo. Purification by columm chromatography on silica gel (100 g) using heptane and ethyl acetate (2:3) as eluent afforded 0.45 g of (1, 1-dimethyl-2-(4-oxo-5-(2'-(N -triphenylmethyltetrazol-5-yl)biphenyl-4-ylmethyl)-2,3,4,5-tetrahydro- 1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)- carbamic acid tert-butyl ester.

Workup

  1. customthe phases were separated
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent was evaporated in vacuo
  4. customPurification by columm chromatography on silica gel (100 g)

Sources & evidence

ORD record
ord-4869f446593941db911bb109f2058444
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

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