Hydrochloric Acid → HCID 86584292, compound

HRID 1957159Notes

Reaction equation

HRID 1957159 reaction equation
[C:1]([O:16][CH:17]([CH2:20][O:21][C:22](=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:18][OH:19])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1.Cl>N1C=CC=CC=1>[C:1]([O:16][CH:17]([CH2:20][O:21][C:22](=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:18][OH:19])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[S:43]([C:40]1[CH:41]=[CH:42][C:37]([CH3:47])=[CH:38][CH:39]=1)([O-:15])(=[O:45])=[O:44]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 892983-Hydroxypropane-1,2-diyl ditetradecanoate

Product 1

HCID 86584292HCID 86584292, compoundYield 131.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2,3 Dimyristoylglycerol (600 mg, 1.4 mmol) was dissolved in pyridine and the solution cooled to 0° C. The solution was stirred under a nitrogen atmosphere and p-toluenesulfonyl chloride (300 mg, 1.57 mmol) was added. The solution was allowed to warm to room temperature and was then stirred overnight at ambient temperature. To the solution was added hydrochloric acid (2.5M, 20 mL) and the solution was extracted three times with methylene chloride (25 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude oil. The oil was purified by flash chromatography (50 g of silica gel, 60 Å) eluting with 5% ethyl acetate/hexane. The oil obtained by flash chromatography was dried under high vacuum at ambient temperature to give 2,3-Dimyristoylglycerol-tosylate(630 mg, 77% yield).

Workup

  1. temperatureto warm to room temperature
  2. stirringwas then stirred overnight at ambient temperature
  3. extractionthe solution was extracted three times with methylene chloride (25 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude oil
  8. customThe oil was purified by flash chromatography (50 g of silica gel, 60 Å)
  9. washeluting with 5% ethyl acetate/hexane
  10. customThe oil obtained by flash chromatography
  11. customwas dried under high vacuum at ambient temperature

Sources & evidence

ORD record
ord-6cbc4758b7a74155af7e38d4f2c4d9f1
Source dataset
uspto-grants-1998_07
Patent number
US05783565

Reaction notes

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