Hexane → HCID 22272745, compound

HRID 1064812Notes

Reaction equation

HRID 1064812 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]([NH:23][C:24]2[C:29]([CH:30]([CH3:32])[CH3:31])=[CH:28][CH:27]=[C:26]([OH:33])[C:25]=2[CH:34]([CH3:36])[CH3:35])=[O:22])[CH2:16][CH2:15]1.[CH:37](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C.CCCCCC>CO.C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]([NH:23][C:24]2[C:29]([CH:30]([CH3:32])[CH3:31])=[CH:28][CH:27]=[C:26]([O:33][CH3:37])[C:25]=2[CH:34]([CH3:36])[CH3:35])=[O:22])[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 22272711HCID 22272711, compound

Product 1

HCID 22272745HCID 22272745, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

2-[4-[3-(Benzoxazol-2-ylthio)propyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide (150 mg, 0.29 mmol) was dissolved in methanol (2 ml) and acetonitrile (3 ml), then N,N-diisopropylethylamine (227 mg, 1.76 mmol) and a solution of trimethylsilyl diazomethane in hexane (2.0M, 0.88 ml, 1.76 mmol) were added thereto and the mixture was stirred for 14 hours. The reaction solution was concentrated, made alkaline with an aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (developing solvent, hexane:acetone=7:3) and the resulting crude crystals were recrystallized from ethyl acetate and hexane to provide 31 mg (yield 20%) of the desired compound as colorless powdery crystals.

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution successively and dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by a silica gel column chromatography (developing solvent, hexane:acetone=7:3)
  7. customthe resulting crude crystals were recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-aa29d3674689471d9787d52eb44a520d
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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