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

HRID 1006135ノート

反応式

HRID 1006135 の反応式
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]

参加物

4

反応物 1

HCID 18337567HCID 18337567、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f0fe6b2dcda246bb8b6ad02864308282
出典データセット
uspto-grants-2004_09
特許番号
US06787559B2

反応ノート

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