Acetic Anhydride → HCID 131726728, compound

HRID 970298Notes

Reaction equation

HRID 970298 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][C@@H:7]([O:20][CH2:21][CH:22]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C@@H:6]1[NH:41][C:42]([O:44]CC(Cl)(Cl)Cl)=O)(=[O:3])[CH3:2].[C:50](OC(=O)C)(=O)C>[Zn]>[C:42]([NH:41][C@@H:6]1[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][C@H:7]1[O:20][CH2:21][CH:22]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:44])[CH3:50]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 131726729HCID 131726729, compound

Product 1

HCID 131726728HCID 131726728, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

tert-Butyl 1-{[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloro-ethoxycarbonyl-amino)-β-D-glucopyranosyloxy]methyl}-(R/S)-undecyl-carbamate 50(27.0 mg, 0.0353 mmol) was dissolved in acetic anhydride (1 ml) into which activated zinc powder (4.6 mg, 0.0706 mmol) had been added. The reaction was stirred for 6 hours, after which it was filtered and evaporated (and co-evaporated with benzene and toluene). The residue was purified by column chromatography to give 51 (11 mg, 49%).

Workup

  1. additionhad been added
  2. filtrationafter which it was filtered
  3. customevaporated (and co-evaporated with benzene and toluene)
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-13567310518a49bb80ad9d9482ec2942
Source dataset
uspto-grants-2007_12
Patent number
US07312194B2

Reaction notes

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