Acetyl chloride → HCID 18175040, compound

HRID 2352311Notes

Reaction equation

HRID 2352311 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([S:17]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=3)(=[O:19])=[O:18])[CH:15]=2)[NH:10][CH:9]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:28]([O:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][S:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][CH:9]=[C:8]3[CH2:7][CH2:6][NH:5][C:1](=[O:3])[CH3:2])(=[O:19])=[O:18])=[CH:26][CH:25]=1)[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19844114HCID 19844114, compound

Product 1

HCID 18175040HCID 18175040, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetyl chloride (0.6 ml) was added dropwise to a stirred solution of the product of Example 4 (3.1 g) in dry dimethylformamide (20 ml) containing triethylamine (3.3 ml) and the resulting suspension stirred at room temperature for 30 min. The suspension was partitioned between hydrochloric acid (2 N, 100 ml) and ethyl acetate (2×100 ml) and the combined extracts were washed with sodium carbonate (2 N, 100 ml) dried (MgSO4) and evaporated in vacuo to give an oil. The oil was purified by flash chromatography eluted with chloroform:methanol (19:1) to give the title compound as a foam (0.8 g), a sample of which (0.4 g) was crystallised from a mixture of ethyl acetate and hexane to give the title compound as a crystalline solid (0.3 g) m.p. 173°-175°.

Workup

  1. customThe suspension was partitioned between hydrochloric acid (2 N, 100 ml) and ethyl acetate (2×100 ml)
  2. washthe combined extracts were washed with sodium carbonate (2 N, 100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto give an oil
  6. customThe oil was purified by flash chromatography
  7. washeluted with chloroform:methanol (19:1)

Sources & evidence

ORD record
ord-e7afdf6c3c284ac9b28e149d488b2ab5
Source dataset
uspto-grants-1989_10
Patent number
US04876267

Reaction notes

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