Acetic Anhydride → HCID 67930798, compound

HRID 728216Notes

Reaction equation

HRID 728216 reaction equation
[N:1]([C@@H:4]1[CH2:9][C@H:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]2[CH2:18][O:19][C@@H:5]1[O:6]2)=[N+]=[N-].C1CCCCC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>CO.[Pd]>[C:26]([NH:1][C@@H:4]1[CH2:9][C@H:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]2[CH2:18][O:19][C@@H:5]1[O:6]2)(=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8079CyclohexeneHCID 86745036HCID 86745036, compound

Product 1

HCID 67930798HCID 67930798, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1,6-anhydro-2-azido-4-O-benzyl-2,3-dideoxy-β-D-ribo-hexopyranose (see Example 13) in methanol (20 ml) was subjected to transfer hydrogenation by heating under reflux with cyclohexene (7 ml) 5% and palladium on charcoal (0.5 g), added in three portions over a period of 6 h. Acetic anhydride (2.5 ml) was then added to the mixture at room temperature. After 2 h, the mixture was filtered, the filtrate was evaporated, and the residue chromatographed on silica gel to yield the title compound as a syrup (0.35 g, 52%), [α]D -28.7°; 13C-nmr data: 101.1 (C-1), 46.4 (C-2), 25.9 (C-3), 74.1 and 73.0 (C-4 and C-5), 65.8 (C-6), 70.5 (PhCH2O), 23.3 (NHCOCH3), 169.2 (NHCOCH3), 137.7 (q-aromatic), 128.5 (×2), 127.9, and 127.5 (×2, aromatic).

Workup

  1. temperatureby heating
  2. additionadded in three portions over a period of 6 h
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated
  5. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-bedd6c6a583446ae83b324f3a9b442e1
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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