4-Chlorobutyryl chloride → tert-butyl (2R)-1-[8-(4-chlorobutanamido)-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylamino]-4-methyl-1-oxopentan-2-ylcarbamate

HRID 1887748Notes

Reaction equation

HRID 1887748 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]([NH:13][C:14](=[O:28])[C@H:15]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:7]2.[Cl:29][CH2:30][CH2:31][CH2:32][C:33](Cl)=[O:34].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:29][CH2:30][CH2:31][CH2:32][C:33]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]([NH:13][C:14](=[O:28])[C@H:15]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:7]2)=[O:34]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 516892Sodium BicarbonateHCID 59620342HCID 59620342, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (2R)-1-(8-amino-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylamino)-4-methyl-1-oxopentan-2-ylcarbamate (300 mg) was dissolved in ethyl acetate (5 mL), and 4-chlorobutyryl chloride (0.1 mL) and saturated aqueous sodium bicarbonate solution (5 mL) were added thereto. The mixture was stirred under cooling on ice for 45 minutes and then subjected to extraction with water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, and was dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (377 mg) was yielded.

Workup

  1. temperatureunder cooling on ice for 45 minutes
  2. extractionsubjected to extraction with water and ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialwas dried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure, whereby the title compound (377 mg)
  6. customwas yielded

Sources & evidence

ORD record
ord-cdd65962eefd4a64aafa85c49c984f99
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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