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

HRID 587930노트

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HRID 587930 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 18930710Methyl 3-(2-(((tert-butoxy)carbonyl)amino)ethyl)benzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
22 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3f9a0ebadb354409ba2a3b4b9b3c09b0
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227918B2

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