Dimethyl Sulfate → Ethyl 4-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)benzoate

HRID 587926ノート

反応式

HRID 587926 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Si]([N-][Si](C)(C)C)(C)C.[Na+].S(OC)(OC)(=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH3:22])[CH2:9][CH2:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 67360059Ethyl 4-(2-(tert-butoxycarbonylamino)ethyl)benzoate

生成物 1

HCID 68475038Ethyl 4-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
22 °C

実験手順

To a solution of 1.25 g (4.26 mmol) of ethyl 4-(2-(tert-butoxycarbonylamino)ethyl)benzoate in 40 mL of dry THF under a nitrogen atmosphere was added dropwise, 4.7 mL (4.7 mmol) of NaHMDS (1.0 M in THF) at 0° C. After stirring for 10 min, 0.50 mL (5.3 mmol) of dimethyl sulfate was added and the reaction was warmed to 22° C. and stirred for about 16 h. The reaction was quenched by adding 25 mL of saturated NaHCO3 and the mixture was extracted with DCM (2×25 mL). The combined organic extracts were dried (Na2SO4) and evaporated and the residue was purified by flash chromatography on silica gel, eluting first with hexane and then gradually increasing to 10% ethyl acetate/hexane to give ethyl 4-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)benzoate as a colorless oil.

後処理

  1. customat 0° C
  2. stirringstirred for about 16 h
  3. customThe reaction was quenched
  4. additionby adding 25 mL of saturated NaHCO3
  5. extractionthe mixture was extracted with DCM (2×25 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customevaporated
  8. customthe residue was purified by flash chromatography on silica gel
  9. washeluting first with hexane
  10. temperaturegradually increasing to 10% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-6408d5a3ec394cee8bc733ed94daa33e
出典データセット
uspto-grants-2016_01
特許番号
US09227918B2

反応ノート

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