Acetyl chloride → HCID 15670345, compound

HRID 1646320Notes

Reaction equation

HRID 1646320 reaction equation
[SH:1][CH:2]([CH3:23])[CH:3]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:5].C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[C:31]([S:1][CH:2]([CH3:23])[CH:3]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:5])(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471Triethylamine2×HCID 15670344HCID 15670344, compound

Product 1

HCID 15670345HCID 15670345, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-[(3-Mercapto-2-benzylbutanoyl)amino]benzoic acid (compound of Example 194) (1.7 g) is suspended in dichloromethane (17 ml), and thereto is added triethylamine (0.52 g)with stirring under ice cooling. To the mixture are further added dropwise acetyl chloride (0.51 g) and triethylamine (0.52 g) simultaneously, and the mixture is stirred at room temperature for one hour. The reaction mixture is diluted with dichloromethane and washed with 10% hydrochloric acid and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then dichloromethane is distilled off under reduced pressure. The residue is dissolved in acetonitrile and purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected and concentrated into dryness under reduced pressure to give the title compound (0.6 g).

Workup

  1. stirringthe mixture is stirred at room temperature for one hour
  2. washwashed with 10% hydrochloric acid and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdichloromethane is distilled off under reduced pressure
  5. dissolutionThe residue is dissolved in acetonitrile
  6. custompurified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
  7. additionThe fractions containing the desired compound
  8. customare collected
  9. concentrationconcentrated into dryness under reduced pressure

Sources & evidence

ORD record
ord-53eb641ffae947ccb2dff67b4a15e9f6
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

Loading…