Acetyl chloride → HCID 59239847, compound

HRID 1668408Notes

Reaction equation

HRID 1668408 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][N:29]5[CH2:34][CH2:33][NH:32][CH2:31][C:30]5=[O:35])=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.[C:36](Cl)(=[O:38])[CH3:37].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C>[C:36]([N:32]1[CH2:33][CH2:34][N:29]([CH2:28][C:25]2[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][N:15]3[C:16](=[O:19])[C:17]4[S:18][C:10]([C:7]5[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=5)=[CH:11][C:12]=4[N:13]=[CH:14]3)=[CH:27][CH:26]=2)[C:30](=[O:35])[CH2:31]1)(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 67360608HCID 67360608, compound

Product 1

HCID 59239847HCID 59239847, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound (30 mg) obtained in Example 38, acetyl chloride (4.7 mg), triethylamine (19 mg) and tetrahydrofuran (2 ml) was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (20 mg) as a colorless powder.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate-hexane (1:1, volume ratio)

Sources & evidence

ORD record
ord-d3935d93c2a04c1fa9a354d690f7fea9
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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