Water → HCID 10521450, compound

HRID 2395205Notes

Reaction equation

HRID 2395205 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([NH:15][C@@H:16]1[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]([OH:20])[C@H:17]1[OH:18])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:27](Cl)(=[O:30])[CH:28]=[CH2:29].O>CO>[C@@H:16]1([N:15]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:27](=[O:30])[CH:28]=[CH2:29])[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]([OH:20])[C@H:17]1[OH:18]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 11130076HCID 11130076, compound

Product 1

HCID 10521450HCID 10521450, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

62.5 mmol (6.63 g) of sodium carbonate are added to 24 mmol (7 g) of N-octyl-β-D-glucopyranosylamine in 100 ml of methanol at 30° C.; 48 mmol (3.9 ml) of acryloyl chloride are run in at 0° C. over 5 minutes into the heterogeneous mixture. The reaction mixture is left at ambient temperature with stirring for 25 minutes. After addition of 100 ml of water and evaporation of the methanol the acrylamidosugar is extracted with 300 ml of ethyl acetate. The organic phase is washed with a saturated solution of NaHCO3. dried over MgSO4 and evaporated at reduced pressure.

Workup

  1. waitThe reaction mixture is left at ambient temperature
  2. extractionis extracted with 300 ml of ethyl acetate
  3. washThe organic phase is washed with a saturated solution of NaHCO3
  4. dry with materialdried over MgSO4
  5. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-3c457038b899464c8a4a6c9e0ced1a2c
Source dataset
uspto-grants-1998_09
Patent number
US05814407

Reaction notes

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