3-Butyn-1-OL → 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[5-(2-hydroxy-ethyl)-isoxazol-3-yl]-benzamide

HRID 1988388Notes

Reaction equation

HRID 1988388 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([CH:20]=[N:21][OH:22])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].[CH2:23]([OH:27])[CH2:24][C:25]#[CH:26].Cl[O-].[Na+]>C(N(CC)CC)C.ClCCl.O>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:26]=[C:25]([CH2:24][CH2:23][OH:27])[O:22][N:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:5]

Participants

7

Reactant 3

HCID 135663-Butyn-1-OLHCID 23665760Sodium HypochloriteHCID 724346312-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(hydroxyimino-methyl)-benzamide

Product 1

HCID 588181972-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[5-(2-hydroxy-ethyl)-isoxazol-3-yl]-benzamideYield 22.1%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(hydroxyimino-methyl)-benzamide (50 mg, 0.15 mmol), but-3-yn-1-ol (27 mg, 0.38 mmol), sodium hypochlorite (1 mL, 4%) and triethylamine (2 drops) in dichloromethane (2 mL) was stirred at room temperature for 5 d. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, and brine, dried over sodium sulfate, filtered and adsorbed onto silica gel. The residue was purified by flash column chromatography (65% ethyl acetate-hexanes) to afford the title compound (13 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe residue was purified by flash column chromatography (65% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-2e8f1e88f85542da8c77d030cd7d72a3
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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