Tetrahydrofuran → Ethyl 2-amino-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate

HRID 1738257노트

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HRID 1738257 반응식
[N:1]([CH:4]([CH:10]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>O>[NH2:1][CH:4]([CH:10]([O:18][Si:19]([C:22]([CH3:23])([CH3:25])[CH3:24])([CH3:21])[CH3:20])[C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 23298343Ethyl 2-azido-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate

생성물 1

HCID 23298326Ethyl 2-amino-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate수율 113%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 5.6 g of ethyl 2-azido-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate (prepared as described in Preparation 77), 7.5 g of triphenylphosphine and 18 ml of a 8:1 by volume mixture of tetrahydrofuran and water was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate and subsequently a 50:1 by volume mixture of methylene chloride and methanol as the eluent, to give 5.9 g of the title compound having Rf=0.59 (on silica gel thin layer chromatography using a 15:1 by volume mixture of methylene chloride and methanol as the developing solvent).

후처리

  1. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation
  2. customThe residue was purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate
  4. additionsubsequently a 50:1 by volume mixture of methylene chloride and methanol as the eluent

출처 및 근거

ORD 기록
ord-78ccf7a8402444e681b2fec028538bdb
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962470

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