HCID 10282284、化合物 → N-[(3S, 7R, 8R, 9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl]-3-(benzyloxy)-4-methoxypyridine-2-carboxamide

HRID 895795ノート

反応式

HRID 895795 の反応式
[H-].C([Al+]CC(C)C)C(C)C.CC(C)C([O:15][C@@H:16]1[C@@H:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:32])[O:22][CH2:21][C@H:20]([NH:33][C:34]([C:36]2[C:41]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[C:40]([O:50][CH3:51])[CH:39]=[CH:38][N:37]=2)=[O:35])[C:19](=[O:52])[O:18][C@H:17]1[CH3:53])=O>C(Cl)Cl>[CH2:25]([C@@H:24]1[C@@H:16]([OH:15])[C@H:17]([CH3:53])[O:18][C:19](=[O:52])[C@@H:20]([NH:33][C:34]([C:36]2[C:41]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[C:40]([O:50][CH3:51])[CH:39]=[CH:38][N:37]=2)=[O:35])[CH2:21][O:22][C:23]1=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

4

反応物 2

HCID 10282284HCID 10282284、化合物HCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 86594190N-[(3S, 7R, 8R, 9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl]-3-(benzyloxy)-4-methoxypyridine-2-carboxamide収率 35%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Diisobutylaluminum hydride (1.0 M in CH2Cl2, 24.8 mmol) was added dropwise to a −78° C. solution of (2) (8.27 mmol, 5.0 g) in CH2Cl2 (40 mL). The mixture was stirred an additional 15 min, quenched with EtOAc (200 mL) and warmed to ambient temperature. Hydrochloric acid (2N, 100 mL) was added slowly and stirred vigorously for 15 min. The layers were separated and the organic layer dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (1% acetic acid/acetone) to give 1.54 g (35%) of 4 as a glassy, white solid, m.p. 110-114° C. 1H-NMR and MS (M+1 535) were consistent with the desired product.

後処理

  1. customquenched with EtOAc (200 mL)
  2. additionHydrochloric acid (2N, 100 mL) was added slowly
  3. stirringstirred vigorously for 15 min
  4. customThe layers were separated
  5. dry with materialthe organic layer dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (1% acetic acid/acetone)

出典と根拠

ORDレコード
ord-6620458615514cd982e0972beca24044
出典データセット
uspto-grants-2005_07
特許番号
US06916932B2

反応ノート

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