Acetyl chloride → HCID 58526179, compound

HRID 1184982Notes

Reaction equation

HRID 1184982 reaction equation
[CH:1]1([NH:7][C:8]([O:16][N:17]2[C:22]([CH3:24])([CH3:23])[CH2:21][CH:20]([O:25][C:26](=[O:28])[CH3:27])[CH2:19][C:18]2([CH3:30])[CH3:29])=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>C1(C)C=CC=CC=1>[C:38]([N:9]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[C:8]([O:16][N:17]1[C:18]([CH3:30])([CH3:29])[CH2:19][CH:20]([O:25][C:26](=[O:28])[CH3:27])[CH2:21][C:22]1([CH3:24])[CH3:23])=[N:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58526184HCID 58526184, compound

Product 1

HCID 58526179HCID 58526179, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of compound 1 (4.21 g, 10 mmol) [prepared according to Example 1] in toluene (25 ml) is added triethylamine (1.55 ml, 11 mmol) and acetyl chloride (0.78 ml, 11 mmol). The mixture is stirred at room temperature for 7 hours, then washed with water (2×10 ml), dried over MgSO4 and evaporated. The residue is chromatographed over silica gel with hexane-ethyl acetate (4:1) and the pure fractions are recristallized from pentane to afford 1.05 g of the title compound as a white solid, mp. 125-130° C.

Workup

  1. washwashed with water (2×10 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue is chromatographed over silica gel with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-7e180cbebb834ecdbf193a00e8d9085c
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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