Sodium Hydroxide → HCID 57595392, 화합물

HRID 1786067노트

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HRID 1786067 반응식
C([O:4][CH2:5][C:6]([N:8]([C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([O:33]C)=[O:32])=[CH:23][CH:22]=2)=[O:20])[C@@H:11]([CH3:37])[CH2:10]1)=[O:7])(=O)C.[OH-].[Na+]>CO.O1CCCC1.O>[Cl:44][C:41]1[CH:40]=[CH:39][C:38]([N:8]([C:6](=[O:7])[CH2:5][OH:4])[C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([OH:33])=[O:32])=[CH:23][CH:22]=3)=[O:20])[C@@H:11]([CH3:37])[CH2:10]2)=[CH:43][CH:42]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 57595487HCID 57595487, 화합물

생성물 1

HCID 57595392HCID 57595392, 화합물수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 21899815MeOH tetrahydrofuran용매

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온도
45 °C

실험 절차

Methyl 5-(4-{[(2S,4R)-4-[[(acetyloxy)acetyl](4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoate (100 mg, 0.16 mmol, 1 eq.) was dissolved in methanol/tetrahydrofuran (2/1) (2 ml). A solution of sodium hydroxide (32 mg, 0.81 mmol, 5 eq.) in water (1 ml) was added and reaction mixture heated to 45° C. for 8 h and at room temperature for 20 h. The mixture was concentrated and the residue was acidified with a 1N HCl aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to give the crude acid. Purification by silica gel chromatography gave pure 5-(4-{[(2S,4R)-4-[(4-chlorophenyl)(glycoloyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoic acid (63 mg, 70%).

후처리

  1. customreaction mixture
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude acid
  9. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-4d8f0399fab14d8e912a54031e081cba
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504508B2

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