Oxygen → (2R)-2-(2-amino-2-methylpropanamido)-N-(8-(2-hydroxy-5-oxopyrrolidin-1-yl)-2-oxo-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl)-4-methylpentanamide

HRID 1887774Notes

Reaction equation

HRID 1887774 reaction equation
[NH2:1][C:2]([CH3:38])([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:8])=[O:4].[O:39]=C1O[C@H]([C@H](CO)O)C(O)=C1O.O=O>C(O)(=O)C.O>[NH2:1][C:2]([CH3:37])([CH3:38])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[C:24](=[O:39])[CH2:23][CH2:22][CH:21]3[OH:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:8])=[O:4]

Participants

6

Reactant 3

HCID 977OxygenHCID 54670067L-Ascorbic AcidHCID 59620332(2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

Product 1

HCID 59620396(2R)-2-(2-amino-2-methylpropanamido)-N-(8-(2-hydroxy-5-oxopyrrolidin-1-yl)-2-oxo-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl)-4-methylpentanamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

(2R)-2-(2-Amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide (1.08 g) was dissolved in acetic acid (30 mL), and a solution of L-(+)-ascorbic acid (3.52 g) and Cu(ClO4)2.6H2O (741 mg) in water (40 mL) was added thereto, followed by stirring at room temperature for 15 minutes while oxygen gas was bubbled into the mixture. Saturated aqueous sodium chloride solution was added to the reaction mixture, and the mixture was washed with ethyl acetate twice. Sodium bicarbonate (88.2 g) was added to the aqueous layer, and the mixture was extracted with chloroform twice. The organic layer was concentrated under reduced pressure, and the thus-recovered residue was purified through chromatography, whereby the title compound (0.5 mg) was yielded.

Workup

  1. customwas bubbled into the mixture
  2. additionSaturated aqueous sodium chloride solution was added to the reaction mixture
  3. washthe mixture was washed with ethyl acetate twice
  4. additionSodium bicarbonate (88.2 g) was added to the aqueous layer
  5. extractionthe mixture was extracted with chloroform twice
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe thus-recovered residue was purified through chromatography, whereby the title compound (0.5 mg)
  8. customwas yielded

Sources & evidence

ORD record
ord-150c346f94c54103b0add4a22cdce0f3
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

Loading…