Sodium hydride → 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

HRID 1887749Notes

Reaction equation

HRID 1887749 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[NH:16][C:15](=[O:18])[CH:14]([NH:19][C:20](=[O:34])[C@H:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:13]2)=[O:6].[H-].[Na+]>CN(C=O)C>[CH3:24][CH:23]([CH3:25])[CH2:22][C@@H:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:20](=[O:34])[NH:19][CH:14]1[CH2:13][C:12]2[C:17](=[C:8]([N:7]3[CH2:2][CH2:3][CH2:4][C:5]3=[O:6])[CH:9]=[CH:10][CH:11]=2)[NH:16][C:15]1=[O:18]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86649077tert-butyl (2R)-1-[8-(4-chlorobutanamido)-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylamino]-4-methyl-1-oxopentan-2-ylcarbamate

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl (2R)-1-[8-(4-chlorobutanamido)-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylamino]-4-methyl-1-oxopentan-2-ylcarbamate (350 mg) was dissolved in N,N-dimethylformaldehyde (4.0 mL), and sodium hydride (34 mg) was added thereto under cooling on ice, followed by stirring for 1.5 hours. The resultant mixture was extracted with water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (325 mg) was yielded.

Workup

  1. temperatureunder cooling on ice
  2. extractionThe resultant mixture was extracted with water and ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure, whereby the title compound (325 mg)
  6. customwas yielded

Sources & evidence

ORD record
ord-7a53d1c8f37e4198a02cd3ba6e1ae17b
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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