Acetic Anhydride → HCID 26470288, compound

HRID 276098Notes

Reaction equation

HRID 276098 reaction equation
[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]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86757832HCID 86757832, compound

Product 1

HCID 26470288HCID 26470288, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-96c465bc8193412481343a91930fbb98
Source dataset
uspto-grants-2002_03
Patent number
US06353095B1

Reaction notes

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