Water → HCID 86743850, compound

HRID 2073258Notes

Reaction equation

HRID 2073258 reaction equation
[C:1]1([S:7]([NH:10][CH:11]2[CH2:15][NH:14][CH2:13][CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CO>[C:23]1([NH:29][C:30]([N:14]2[CH2:15][CH:11]([NH:10][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH2:12][CH2:13]2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 18337228HCID 18337228, compound

Product 1

HCID 86743850HCID 86743850, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2S,4R)-2-[(E and Z)-5-carboxy-1-pentenyl]-4-phenylsulfonylaminopyrrolidine (169 mg), triethylamine (0.070 ml) and phenyl isocyanate (0.060 ml) in methanol (5 ml) was stirred at room temperature overnight and water was added to the solution. The solution was extracted with chloroform and organic phase was washed with brine. After the solution was dried over magnesium sulfate, the solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of chloroform and methanol (40:1) as an eluent to give (2S,4R)-2-[(E and Z)-5-carboxy-1-pentenyl]-1-phenylcarbamoyl-4-phenylsulfonylaminopyrrolidine (51 mg) as an oil.

Workup

  1. extractionThe solution was extracted with chloroform and organic phase
  2. washwas washed with brine
  3. dry with materialAfter the solution was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customthe residue was chromatographed on a silica gel column with a mixture of chloroform and methanol (40:1) as an eluent

Sources & evidence

ORD record
ord-bb02e745ca9f42489504101f5ffe5add
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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