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

HRID 53330ノート

反応式

HRID 53330 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b047db079ee84a9d98cbc5b907eb38f1
出典データセット
uspto-grants-1997_04
特許番号
US05618941

反応ノート

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