Sodium Bicarbonate → HCID 70401798, compound

HRID 986188Notes

Reaction equation

HRID 986188 reaction equation
[P:1]([O-:44])([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][N:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1)([O:3][CH2:4][CH:5]([O:26][C:27](=[O:32])[CH2:28][C:29]([CH3:31])=[O:30])[CH2:6][O: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][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:2].[C:45](=O)([O-])O.[Na+]>CC(C)=O>[P:1]([O-:44])([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][N+:39]1([CH3:45])[CH2:43][CH2:42][CH2:41][CH2:40]1)([O:3][CH2:4][CH:5]([O:26][C:27](=[O:32])[CH2:28][C:29]([CH3:31])=[O:30])[CH2:6][O: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][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20159382HCID 20159382, compound

Product 1

HCID 70401798HCID 70401798, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To 30 ml of acetone was dissolved 1.17 g (1.8 mmole) of 2-(acetoacetyloxy)-3-(octadecyloxy)propyl 5-(pyrrolidino)pentyl phosphate, and 820 mg (10 mmole) of sodium hydrogen-carbonate previously crushed in a mortar and 410 mg (2.2 mmole) of methyl para-tolanesulrte were added to the solution. The mixture was stirred at 50° C. for 13 hours and acetone was distilled off under reduced pressure. In 30 ml of water was dissolved the residue and the solution was adjusted to pH 4 with 2N HCl, followed by extraction with a mixture of dichloromethane and ethanol (10:1). The solvent was distilled off and the residue was purified by silica gel column chromatography [chloroform-methanol-water (65:25:4)] to give 550 mg yield: 46%) of the desired compound.

Workup

  1. custompreviously crushed in a mortar and 410 mg (2.2 mmole) of methyl para-tolanesulrte
  2. additionwere added to the solution
  3. distillationacetone was distilled off under reduced pressure
  4. dissolutionIn 30 ml of water was dissolved the residue
  5. extractionfollowed by extraction with a mixture of dichloromethane and ethanol (10:1)
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography [chloroform-methanol-water (65:25:4)]

Sources & evidence

ORD record
ord-fc7b09b767924587b38866d453998c8e
Source dataset
uspto-grants-1987_12
Patent number
US04710579

Reaction notes

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