Acetyl chloride → HCID 178501350, compound

HRID 1728477Notes

Reaction equation

HRID 1728477 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]([C@@H:9]1[NH:12][C:11](=[O:13])[C@H:10]1[CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])=[N:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:8].C(N(CC)CC)C>C(Cl)Cl>[CH3:5][O:6][C:7]([C@@H:9]1[N:12]([C:1](=[O:3])[CH3:2])[C:11](=[O:13])[C@H:10]1[CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])=[N:19][C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])=[O:8]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178501360HCID 178501360, compound

Product 1

HCID 178501350HCID 178501350, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (9.5 g, 0.12 mol) was added to a -10° C. methylene chloride (50 mL) solution of compound 7 (2.0 g, 4.0 mmol). Triethylamine (12.3 g, 0.12 mol) was added dropwise with vigorous stirring of the reaction mixture. After the addition was complete, the resultant suspension was stirred for an additional 2 h at room temperature and then washed with H2O. The organic phase was separated, washed with saturated aqueous NaHCO3 solution, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (CH2Cl2 :MeOH/99.5:0.5) to afford 700 mg (36%) of the title product.

Workup

  1. additionAfter the addition
  2. washwashed with H2O
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (CH2Cl2 :MeOH/99.5:0.5)

Sources & evidence

ORD record
ord-dc869814c8e84faf80977ab0e711c844
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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