N-benzyloxy 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionamide → N-hydroxy-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionamide

HRID 1760814ノート

反応式

HRID 1760814 の反応式
C([O:8][NH:9][C:10](=[O:42])[C@H:11]([N:18]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]2[O:39][CH2:40][O:41][C:35]=2[CH:34]=1)[S:19]([C:22]1[C:27]([CH3:28])=[CH:26][C:25]([O:29][CH3:30])=[CH:24][C:23]=1[CH3:31])(=[O:21])=[O:20])[CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])C1C=CC=CC=1>[Pd].C(O)C.O1CCCC1>[OH:8][NH:9][C:10](=[O:42])[C@H:11]([N:18]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]2[O:39][CH2:40][O:41][C:35]=2[CH:34]=1)[S:19]([C:22]1[C:23]([CH3:31])=[CH:24][C:25]([O:29][CH3:30])=[CH:26][C:27]=1[CH3:28])(=[O:20])=[O:21])[CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15]

参加物

4

反応物 1

HCID 18337566N-benzyloxy 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionamide

生成物 1

HCID 9849880N-hydroxy-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionamide収率 44.8%

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-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionamide (580 mg, 0.94 mmol) in a 3:1 mixture of ethanol/tetrahydrofuran (30 ml) was added 10% palladium on charcoal (60 mg). The reaction mixture was placed under a hydrogen balloon and stirred for 6 hours. The material was filtered through a short plug of silica, rinsing with ethanol (200 ml). The filtrate was condensed on the roto-evaporator and the residue was purified by preparative thin layer chromatography using 8.5% methanol-methylene chloride as eluant providing N-hydroxy-2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionamide as a tan powder (223 mg).

後処理

  1. filtrationThe material was filtered through a short plug of silica
  2. washrinsing with ethanol (200 ml)
  3. customcondensed
  4. customon the roto-evaporator
  5. customthe residue was purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-691a8296997c444f8ab9809bb8b3c328
出典データセット
uspto-grants-2005_01
特許番号
US06844366B2

反応ノート

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