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Sodium hydride → 3-t-Butoxycarbonylamino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-(2-thienyl)[1,1'-biphenyl]-4-yl]methyl]-1H-1-benzazepin-3(R)-yl]-butanamide

HRID 1080726
Notes
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Reaction equation

HRID 1080726 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@@H:14]1[CH2:20][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[NH:16][C:15]1=[O:25])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:44]2[S:45][CH:46]=[CH:47][CH:48]=2)=[CH:34][CH:33]=1>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:27])([CH3:26])[CH2:10][C:11]([NH:13][C@@H:14]1[CH2:20][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:44]3[S:45][CH:46]=[CH:47][CH:48]=3)=[CH:36][CH:37]=2)[C:15]1=[O:25])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 104746043-t-butoxycarbonylamino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamideHCID 23365403HCID 23365403, compound

Product 1

HCID 228679293-t-Butoxycarbonylamino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-(2-thienyl)[1,1'-biphenyl]-4-yl]methyl]-1H-1-benzazepin-3(R)-yl]-butanamide

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 174 mg (0.465 mmol) of 3-t-butoxycarbonylamino-3-methyl-N-[2,3,4,5-tetrahydro-2oxo-1H-1-benzazepin-3(R)-yl]-butanamide (Example 1, Step I) in 3.0 mL of dry dimethylformamide was treated with 22.2 mg of 60% sodium hydride oil dispersion (13.3 mg NaH, 0.558 mmol, 1.2 eq). The reaction mixture was stirred at room temperature for 30 minutes. To the solution was added 153 mg (0.465 mmol) of a solution of 4-bromomethyl-2'-(2-thienyl)-1,1'-biphenyl dissolved in 3 mL of dry dimethylformamide. After stirring at room temperature for 3 hours, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water (4×), dried over magnesium sulfate, filtered and evaporated under vacuum. The residue was purified by chromatography on silica gel, eluting with hexane/ethyl acetate (1:1) to give 160 mg of the product.

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. washThe organic layer was washed with water (4×)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-8415a4abf050489fa06acbd0dfe65bd5
Source dataset
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05583130

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes