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Sodium hydride → tert-butyl (2R)-4-methyl-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(pyridin-2-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino]pentan-2-ylcarbamate

HRID 2070152
Notes
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Reaction equation

HRID 2070152 reaction equation
[CH3:1][CH:2]([CH3:33])[CH2:3][C@@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:5](=[O:24])[NH:6][CH:7]1[CH2:16][C:15]2[C:10](=[C:11]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:23].Br.Br[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1.[H-].[Na+]>CN(C=O)C>[CH3:1][CH:2]([CH3:33])[CH2:3][C@@H:4]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:5](=[O:24])[NH:6][CH:7]1[CH2:16][C:15]2[C:10](=[C:11]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[C:8]1=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 70821488tert-butyl (2R)-4-methyl-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolin-3-ylamino]pentan-2-ylcarbamate

Product 1

HCID 70821489tert-butyl (2R)-4-methyl-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(pyridin-2-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino]pentan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl (2R)-4-methyl-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolin-3-ylamino]pentan-2-ylcarbamate (320 mg) was dissolved in N,N-dimethylformaldehyde (4.0 mL), and 2-bromomethylpyridine hydrobromide (216 mg) and sodium hydride (67 mg) were added thereto under cooling on ice, followed by stirring for one hour. The resultant mixture was subjected to extraction with saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the thus-recovered residue was purified through silica gel column chromatography (ethyl acetate:methanol=20:1), whereby the title compound (315 mg) was yielded.

Workup

  1. temperatureunder cooling on ice
  2. extractionThe resultant mixture was subjected to extraction with saturated aqueous ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe thus-recovered residue was purified through silica gel column chromatography (ethyl acetate:methanol=20:1), whereby the title compound (315 mg)
  7. customwas yielded

Sources & evidence

ORD record
ord-05abbe22b66b4eaf872dca533d4ac0e7
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08299255B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes