Triethylamine → HCID 18979144, compound

HRID 2393193Notes

Reaction equation

HRID 2393193 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:18]2[C:19](=[O:30])[C:20]3[C:25]([C:26](=[O:29])[C:27]=2[CH3:28])=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][OH:17])=[O:15])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:41])[CH2:39][CH3:40]>C1COCC1>[C:38]([O:17][NH:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:18]1[C:19](=[O:30])[C:20]2[C:25]([C:26](=[O:29])[C:27]=1[CH3:28])=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:41])[CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 9822660HCID 9822660, compound

Product 1

HCID 18979144HCID 18979144, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-methoxyphenyl)-6-(3-methyl-1,4-naphthoquinon-2-yl)hexanohydroxamic acid (2.8 g) in THF (40 ml) was added triethylamine (1.4 ml) followed by addition of propionyl chloride (669 mg) at 0° C. The reaction mixture was stirred for 1 hour and partitioned between water and ethyl acetate. The organic layer was dried and concentrated. The residue was purified with silica gel chromathography using hexane-ethyl acetate as an eluent to give the titled compound (2.1 g).

Workup

  1. custompartitioned between water and ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified with silica gel chromathography

Sources & evidence

ORD record
ord-92ba6d9cf9d5408e96eae079bb32bc1d
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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