Tetrahydrofuran → N4-Hydroxy-2-isobutyl-N1-(9-oxo-1,8-diaza-tricyclo(10.6.1.013,18)nonadeca-12(19),13,15,17-tetraen-10-YL)-succinamide

HRID 849729ノート

反応式

HRID 849729 の反応式
C([O:8][NH:9][C:10](=[O:40])[CH2:11][C@H:12]([C:17](=[O:39])[NH:18][C@H:19]1[CH2:36][C:35]2=[CH:37][N:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=32)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]1=[O:38])[CH2:13][CH:14]([CH3:16])[CH3:15])C1C=CC=CC=1.C1COCC1>C(O)C.[Pd]>[OH:8][NH:9][C:10](=[O:40])[CH2:11][C@H:12]([C:17](=[O:39])[NH:18][C@H:19]1[CH2:36][C:35]2=[CH:37][N:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=32)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]1=[O:38])[CH2:13][CH:14]([CH3:16])[CH3:15]

参加物

5

反応物 2

HCID 8028TetrahydrofuranHCID 86752868(3R,10S)-N-benzyloxy-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6. 1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanamide

生成物 1

HCID 478379N4-Hydroxy-2-isobutyl-N1-(9-oxo-1,8-diaza-tricyclo(10.6.1.013,18)nonadeca-12(19),13,15,17-tetraen-10-YL)-succinamide収率 92%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Alternatively, (3R,10S)-N-benzyloxy-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6. 1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanamide (1.0 g, 1.83 mmol) was taken up in a solution of 20% THF in ethanol (500 mL) and then Pd on activated charcoal (200 mg) was added portionwise. The resulting slurry was stirred as H2 gas was gently bubbled through the solution. After 4 hours, the reaction mixture was suction filtered through a bed of celite (1.5 cm), and the filtrate was concentrated and then taken up in methanol (30 mL) and filtered through a plug of cotton. Recrystallization from methanol/ethyl acetate/ether/petroleum ether gave (3R,10S)-N-hydroxy-5-methyl-3-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-yl-carbamoyl)hexanamide (768 mg, 92%), MS: 455 (M-H)+.

後処理

  1. customwas gently bubbled through the solution
  2. filtrationfiltered through a bed of celite (1.5 cm)
  3. concentrationthe filtrate was concentrated
  4. filtrationfiltered through a plug of cotton
  5. customRecrystallization from methanol/ethyl acetate/ether/petroleum ether

出典と根拠

ORDレコード
ord-c8847b739da14f62b170078bea30e936
出典データセット
uspto-grants-2000_01
特許番号
US06013792

反応ノート

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