Oxalyl chloride → HCID 15712740, compound

HRID 703515Notes

Reaction equation

HRID 703515 reaction equation
[CH:1]([CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C:5]([OH:7])=O)([CH3:3])[CH3:2].[C:22](Cl)(=[O:26])[C:23](Cl)=O>>[CH:1]([CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[C:5]([N:19]1[CH2:16][CH2:15][CH2:14][C@H:23]1[CH2:22][OH:26])=[O:7])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 65578Oxalyl chlorideHCID 15712739HCID 15712739, compound

Product 1

HCID 15712740HCID 15712740, compound

Procedure

Oxalyl chloride (10 ml) was added to 2-isopropyl-7-(p-nitrophenyl)heptanoic acid (200 mg; prepared in reference example 6). The solution was stirred for 10 mins, and concentrated to dryness. Methylene chloride (10 ml) was added to this residue followed by the addition of 2-hydroxymethylpyrrolidine (0.087 ml). The solution was cooled with ice. Triethylamine (0.143 ml) was added to this reaction solution. The solution was stirred for 30 mins. Subsequently, the reaction solution was evaporated. The residue was purified by column chromatography on silica gel to give the title compound (150 mg) having the following physical data:

Workup

  1. concentrationconcentrated to dryness
  2. additionMethylene chloride (10 ml) was added to this residue
  3. additionfollowed by the addition of 2-hydroxymethylpyrrolidine (0.087 ml)
  4. temperatureThe solution was cooled with ice
  5. additionTriethylamine (0.143 ml) was added to this reaction solution
  6. stirringThe solution was stirred for 30 mins
  7. customSubsequently, the reaction solution was evaporated
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6eb4fc4444454f28968be973ebde7342
Source dataset
uspto-grants-1991_01
Patent number
US04983624

Reaction notes

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