Acetic Anhydride → HCID 26470288, 화합물

HRID 276098노트

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HRID 276098 반응식
[N:1]([C@@H:4]1[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:12]([O:18][C:19](=[O:21])[CH3:20])[C@H:11]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:10][C@@H:5]1[O:6][C:7](=[O:9])[CH3:8])=[N+]=[N-].[CH3:27][C:28](OC(C)=O)=[O:29]>[Pd]>[C:28]([NH:1][C@@H:4]1[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:12]([O:18][C:19](=[O:21])[CH3:20])[C@H:11]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:10][C@@H:5]1[O:6][C:7](=[O:9])[CH3:8])(=[O:29])[CH3:27]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 86757832HCID 86757832, 화합물

생성물 1

HCID 26470288HCID 26470288, 화합물수율 83%

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

A solution of Compound 9 (0.60 g, 1.62 mmol) in Ac2O (20 mL) was hydrogenated over 70 mg of 10 percent palladium on charcoal under atmospheric pressure. After 10 hours, the solution was filtered and the filtrate was concentrated in vacuo. By flash column chromatography with EtOAc-toluene (2.5:1), 0.52 g of Compound 10 was obtained in 83 percent yield. 1H NMR (CDCl3) δ6.03 (1H, d, J1-2=1.5 Hz, H-1), 5.34 (1H, dd, J3-4=10.0 Hz, J3-2=5.0 Hz, H-3), 5.18 (1H, t, J4-5=J4-3=10.0 Hz, H-4), 4.65 (1H, ddd, J5-4=10.0 Hz, J5-6a=5.0 Hz, J5-6b=2.0 Hz, H-5), 4.29 (1H, dd, J6a-6b12.5 Hz, J6a-5b=5 Hz, H-6a), 4.06 (1H, dd, J2-3=5.0 Hz, J2-1=1.5 Hz, H-2), 4.05 (1H, dd, J6b-6a=12.5 Hz, J6b-5=2.0 Hz, H-6b), 2.18 (3H, s, acetyl), 2.10 (3H, s, acetyl), 2.07 (3H, s, acetyl), 2.07 (3H, s, acetyl), 2.01 (3H, s, acetyl). 13C NMR (CDCl3) δ170.4, 170.1, 170.0, 169.6, 168.0, 91.7, 73.4, 70.1, 65.5, 62.1, 49.3, 23.2, 20.8, 20.7, 20.7, 20.6. HRMS (FAB) calcd for C16H23NO10Na (M+Na+) 412.1220, found 412.1224.

후처리

  1. filtrationthe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-96c465bc8193412481343a91930fbb98
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353095B1

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