Dimethyl Sulfoxide → HCID 10623062, compound

HRID 1292539Notes

Reaction equation

HRID 1292539 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=1)[C:11]([NH:13][C@H:14]([C:22]([N:24]1[CH2:30][CH2:29][CH2:28][C@H:25]1[CH2:26][OH:27])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.CS(C)=O>O>[O:1]([C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=1)[C:11]([NH:13][C@H:14]([C:22]([N:24]1[CH2:30][CH2:29][CH2:28][C@H:25]1[CH:26]=[O:27])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 10527268HCID 10527268, compound

Product 1

HCID 10623062HCID 10623062, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 216.4 mg of N-(N-(3-phenoxybenzoyl)-L-phenylalanyl)-L-prolinol were added 0.92 ml of acetic anhydride and 2.6 ml of DMSO. The mixture was stirred at room temperature for 22 hours. Then 40 ml of water was added to the reaction mixture. After stirring for an hour, the mixture was extracted 3 times with 20 ml each of dichloromethane. The oily layer was dried over anhydrous sodium sulfate and the solvent was distilled off to give 248.7 mg of an oily substance. The oily substance was purified by column chromatography (silica gel, developed with hexane-ethyl acetate) to give 85.5 mg of an amorphous solid. The solid was further purified by column chromatography (silica gel, developed with dichloromethane-ethyl acetate) to give 46.4 mg of the title compound as a colorless transparent amorphous solid. Yield, 21.5%.

Workup

  1. stirringAfter stirring for an hour
  2. extractionthe mixture was extracted 3 times with 20 ml each of dichloromethane
  3. dry with materialThe oily layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customto give 248.7 mg of an oily substance
  6. customThe oily substance was purified by column chromatography (silica gel, developed with hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7e0538e4541d4c15ac4dd7f9215de64c
Source dataset
uspto-grants-1998_05
Patent number
US05756763

Reaction notes

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