HCID 10282284, 화합물 → 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 895795노트

반응식

HRID 895795 반응식
[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

참가 물질

4

반응물 2

HCID 10282284HCID 10282284, 화합물HCID 21225700Diisobutylaluminumhydride

생성물 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-carboxamide수율 35%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6620458615514cd982e0972beca24044
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916932B2

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