Sodium Carbonate → HCID 10670262, compound

HRID 2395206Notes

Reaction equation

HRID 2395206 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([NH:21][C@@H:22]1[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]1[OH:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:33](Cl)(=[O:36])[CH:34]=[CH2:35]>O.C1COCC1>[C@@H:22]1([N:21]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:33](=[O:36])[CH:34]=[CH2:35])[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]1[OH:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 10667206HCID 10667206, compound

Product 1

HCID 10670262HCID 10670262, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 85 mmol (9 g) of sodium carbonate in 25 ml of water is added to a solution of 13.7 mmol (4 g) of N-tetradecyl-β-D-glucopyranosylamine in 190 ml of THF. A solution of 26 mmol (2.0 ml) of acryloyl chloride in 20 ml of THF is added dropwise over one hour. The THF is evaporated off and the acylamidosugar is then 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. customThe THF is evaporated off
  2. extractionthe acylamidosugar is then 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-0091a6309a0445199a85fc3ada3181bc
Source dataset
uspto-grants-1998_09
Patent number
US05814407

Reaction notes

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