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

HRID 53330Notes

Reaction equation

HRID 53330 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b047db079ee84a9d98cbc5b907eb38f1
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

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