Acetyl chloride → HCID 23447981, compound

HRID 366368Notes

Reaction equation

HRID 366368 reaction equation
Cl.Cl.[N:3]1([CH:9]([C:16]2[CH:28]=[CH:27][C:19]([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[C:36]([Cl:39])(=[O:38])[CH3:37]>C(Cl)Cl>[ClH:39].[C:36]([N:6]1[CH2:7][CH2:8][N:3]([CH:9]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[O:21])=[CH:27][CH:28]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:4][CH2:5]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23447948HCID 23447948, compound

Product 1

HCID 23447981HCID 23447981, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The free amine of compound 64 (100 mg, 0.28 mmol) was dissolved in methylene chloride (5 ml), cooled to 0° C. Triethyl amine (43 μl, 0.31 mmol) was added and then acetyl chloride (22 μl, 0.31 mmol) was added dropwise. After 10 min, the solution was washed with potassium carbonate (10%), dried (K2CO3) and evaporated in vacuo. The residue was purified by chromatography on silica (CH2Cl2 /MeOH/NH3, 95:5:0.5) to give 116 mg of compound 77 (~100 %).

Workup

  1. washthe solution was washed with potassium carbonate (10%)
  2. dry with materialdried (K2CO3)
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica (CH2Cl2 /MeOH/NH3, 95:5:0.5)

Sources & evidence

ORD record
ord-cd3f534317e24a1597555611987224ef
Source dataset
uspto-grants-2000_10
Patent number
US06130222

Reaction notes

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