Water → Methyl 3-(2-(((tert-butoxy)carbonyl)amino)ethyl)benzoate

HRID 587930ノート

反応式

HRID 587930 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O.O>O1CCCC1>[C:18]([O:17][C:15]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:14])([CH3:21])([CH3:20])[CH3:19]

参加物

5

反応物 3

HCID 962WaterHCID 90495Di-tert-butyl dicarbonateHCID 10511548Methyl 3-(2-aminoethyl)benzoate

生成物 1

HCID 18930710Methyl 3-(2-(((tert-butoxy)carbonyl)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 5.12 g (28.6 mmol) of methyl 3-(2-aminoethyl)benzoate in 71 mL tetrahydrofuran (THF) was added 7.48 g (34.3 mmol) of BOC2O. The mixture was stirred for about 16 h at 22° C. and 100 mL of water was added. The mixture was extracted with ethyl acetate (2×100 mL) and the organic phase was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography on silica gel, eluting first with hexane and then gradually increasing to 20% ethyl acetate/hexane to give methyl 3-(2-(tert-butoxycarbonylamino)ethyl)benzoate which was further converted to 2d in a manner analogous to Method B.

後処理

  1. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting first with hexane
  7. temperaturegradually increasing to 20% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-3f9a0ebadb354409ba2a3b4b9b3c09b0
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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