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 2070178노트

반응식

HRID 2070178 반응식
[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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-6a186aa4d40c478bb92d873e197b343f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299255B2

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