pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate → pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate

HRID 2230406ノート

反応式

HRID 2230406 の反応式
C(OC([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:49][OH:50])[C@@H:21]([OH:48])[C@@H:22]([OH:47])[C@H:23]([OH:46])[C:24]([NH:26][C@H:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:28][C:29]([O:31][CH2:32][O:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:30])=[O:25])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=O)C1C=CC=CC=1>CO.[Pd]>[OH:46][C@@H:23]([C@H:22]([OH:47])[C@H:21]([OH:48])[C@@H:20]([NH:19][C:17](=[O:18])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH2:11])[CH2:49][OH:50])[C:24]([NH:26][C@H:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:28][C:29]([O:31][CH2:32][O:33][C:34](=[O:39])[C:35]([CH3:36])([CH3:37])[CH3:38])=[O:30])=[O:25]

参加物

4

反応物 1

HCID 53899016pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate

生成物 1

HCID 59902696pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate収率 83.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (150 mg) in methanol (5 ml) was added 10% palladium on activated carbon (30 mg) and the mixture was stirred under hydrogen atmosphere at room temperature for 1.5 hours. After removal of the catalyst by filtration, the filtrate was concentrated under reduced pressure. Recrystallization from ethyl acetate-hexane provided the title compound (101 mg).

後処理

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customRecrystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-f5a57a547ddc477f81e2908cd3af265c
出典データセット
uspto-grants-2002_07
特許番号
US06423869B1

反応ノート

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