HCID 18337567, 화합물 → N-hydroxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3(S)-hydroxybutyramide

HRID 1760823노트

반응식

HRID 1760823 반응식
C([O:8][NH:9][C:10](=[O:40])[C@H:11]([N:15]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]2[O:37][CH2:38][O:39][C:33]=2[CH:32]=1)[S:16]([C:19]1[C:24]([CH3:25])=[CH:23][C:22]([O:26][CH3:27])=[C:21]([CH3:28])[C:20]=1[CH3:29])(=[O:18])=[O:17])[C@@H:12]([OH:14])[CH3:13])C1C=CC=CC=1>[Pd].C(O)C.O1CCCC1>[OH:8][NH:9][C:10](=[O:40])[C@H:11]([N:15]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]2[O:37][CH2:38][O:39][C:33]=2[CH:32]=1)[S:16]([C:19]1[C:24]([CH3:25])=[CH:23][C:22]([O:26][CH3:27])=[C:21]([CH3:28])[C:20]=1[CH3:29])(=[O:18])=[O:17])[C@@H:12]([OH:14])[CH3:13]

참가 물질

4

반응물 1

HCID 18337567HCID 18337567, 화합물

생성물 1

HCID 18337574N-hydroxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3(S)-hydroxybutyramide수율 63.7%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

To a solution of N-benzyloxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3(S)-hydroxybutyramide (1.25 g, 2.19 mmol) in argon deoxygenated 80% ethanol-tetrahydrofuran (100 mL) was added 10% Pd—C (0.7 g), and the resulting mixture was hydrogenated at atmospheric pressure for 60 min. The reaction mixture was degassed under argon and the slurry was filtered over Celite. The Celite cake was washed with ample 80% ethanol-methylene chloride and the filtrate was concentrated to almost dryness. The mixture was dissolved in 4 mL of ethyl acetate which was added slowly dropwise to 100 mL of vigorously stirring hexanes. The slurry was filtered to afford N-hydroxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3(S)-hydroxybutyramide (0.67 g) as a white solid.

후처리

  1. customThe reaction mixture was degassed under argon
  2. filtrationthe slurry was filtered over Celite
  3. washThe Celite cake was washed with ample 80% ethanol-methylene chloride
  4. concentrationthe filtrate was concentrated to almost dryness
  5. dissolutionThe mixture was dissolved in 4 mL of ethyl acetate which
  6. additionwas added slowly dropwise to 100 mL of vigorously stirring hexanes
  7. filtrationThe slurry was filtered

출처 및 근거

ORD 기록
ord-90625ec3aca44abdb8dff5b0ee2c346e
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844366B2

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