tert-Butanol → Ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

HRID 53330노트

반응식

HRID 53330 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11](CCC([O-])=O)[CH:12]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=2)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.C([N:46]([CH2:49]C)[CH2:47][CH3:48])C.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>>[C:51]([O:55][C:49]([NH:46][CH2:47][CH2:48][C:11]1[CH:12]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:10]=1)=[O:34])([CH3:54])([CH3:53])[CH3:52]

참가 물질

5

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86750692Monoethyl 5-[(4-fluorophenyl)-methyl]-1,3-benzenedipropanoate

생성물 1

HCID 19962360Ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

실험 절차

A solution of monoethyl 5-[(4-fluorophenyl)-methyl]-1,3-benzenedipropanoate (3.0 g), diphenyl-phosphoryl azide (2.51 g) and triethylamine (1.3 ml) in dry t-butanol (25 ml) was stirred at room temperature for 15 minutes and then heated under reflux for 20 hours. The solution was evaporated and the residue was partitioned between ether and wateT. The ether layer was separated, dried (MgSO4) and evaporated to give an oil which was chromatographed on silica gel. Elution with dichloromethane gave the title compound as a gum (2.41 g), Rf 0.2(SS 3). N.M.R. δ(CDCl3): 1.23(3H,t), 1.44(9H,s), 2.58(2H,t), 2.72(2H,t), 2.88(2H,t), 3.32(2H,m), 3.89(2H,s), 4.10(2H,q), 4.50(1H,br), 6.82-6.90(3H), 6.94-7.0(2H,m), 7.09-7.15(2H,m).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. customThe solution was evaporated
  4. customthe residue was partitioned between ether and wateT
  5. customThe ether layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give an oil which
  9. customwas chromatographed on silica gel
  10. washElution with dichloromethane

출처 및 근거

ORD 기록
ord-b047db079ee84a9d98cbc5b907eb38f1
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618941

반응 노트

불러오는 중…