Acetyl chloride → HCID 18660148, compound

HRID 1292694Notes

Reaction equation

HRID 1292694 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C@@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:13][CH2:14][CH3:15].C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[C:20]([O:19][C:17]([NH:16][C@@H:11]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][N:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1])[C:31](=[O:33])[CH3:32])=[O:18])([CH3:22])([CH3:21])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10615682Carbamic acid, [(1S)-1-[[(2,3-dimethylphenyl)amino]methyl]pentyl]-, 1,1-dimethylethyl ester

Product 1

HCID 18660148HCID 18660148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of Step H (500 mg, 1.56 mmol) and triethylamine (0.240 mL, 1.72 mmol) in 10 mL of dichloromethane at 0° C. was added acetyl chloride (0.122 mL, 1.72 mmol). After 20 min, the solution was warmed to room temperature, then stirred another 2 hours. The reaction was poured into CH2Cl2, washed with 10% citric acid and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product.

Workup

  1. washwashed with 10% citric acid and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2601bc1cabd4278867ed49d3c2e3c95
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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