Acetic Anhydride → HCID 86691699, compound

HRID 1022468Notes

Reaction equation

HRID 1022468 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH:12]([OH:14])[C@@H:11]([OH:15])[C@H:10]([OH:16])[C@H:9]2[OH:17])=[CH:4][C:3]=1[CH2:18][C:19]1[CH:28]=[CH:27][C:22]2[O:23][CH2:24][CH2:25][O:26][C:21]=2[CH:20]=1.C(O[C:33](=[O:35])[CH3:34])(=O)C>N1C=CC=CC=1>[C:12]([O:15][C@H:11]1[C@H:10]([O:16][C:10](=[O:16])[CH3:9])[C@@H:9]([O:17][C:22](=[O:23])[CH3:21])[C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]4[O:23][CH2:24][CH2:25][O:26][C:21]=4[CH:20]=3)[CH:4]=2)[O:13][CH:12]1[O:14][C:33](=[O:35])[CH3:34])(=[O:13])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70873313HCID 70873313, compound

Product 1

HCID 86691699HCID 86691699, compoundYield 113.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled solution of (3S,4R,5R,6S)-6-[4-bromo-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-tetrahydro-pyran-2,3,4,5-tetraol (4.7 g, 9.9 mmol) in pyridine (20 ml) was added acetic anhydride (8.1 g, 79.5 mmol) at 0° C. After complete addition reaction mixture was stirred at room temperature for 2 h. Pyridine was evaporated under reduced pressure. The resulting residue was taken in ethyl acetate and washed with aqueous 1 N sodium bisulfate solution followed by brine, dried over sodium sulfate, concentrated to give 3.5 g of acetic acid (3S,4R,5S,6S)-3,4,5-triacetoxy-6-[4-bromo-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-tetrahydro-pyran-2-yl ester.

Workup

  1. additionAfter complete addition reaction mixture
  2. customPyridine was evaporated under reduced pressure
  3. washwashed with aqueous 1 N sodium bisulfate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9314f44f53b24a06a918cd9c09ce0652
Source dataset
uspto-grants-2014_05
Patent number
US08722633B2

Reaction notes

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