tert-Butanol → HCID 10621626, compound

HRID 725034Notes

Reaction equation

HRID 725034 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH2:21][CH2:22]C(O)=O)[CH:11]=[C:12]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=1)=[O:5])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.C([N:45]([CH2:48]C)CC)C.[C:50]([OH:54])([CH3:53])([CH3:52])[CH3:51]>>[C:50]([O:54][C:48]([NH:45][CH2:22][CH2:21][C:10]1[CH:9]=[C:8]([CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:13]=[C:12]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=1)=[O:33])([CH3:53])([CH3:52])[CH3:51]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 10569218HCID 10569218, compound

Product 1

HCID 10621626HCID 10621626, compound

Procedure

A solution of 3-[3-(2-ethoxycarbonylethyl)-5-(3-pyridylmethyl)phenyl]propanoic acid (Preparation 31; 4.89), diphenylphosphoryl azide (3.94 g) and triethylamine (1.45 g) in t-butanol (50 ml) was heated under reflux for 18 hours and then evaporated under vacuum. The residue was chromatographed on silica gel using dichloromethane:methanol (50:l) as eluent. After elution of some impurity, the product fractions were obtained; these were combined and evaporated under vacuum to give the title compound as an oil (3.60 g); Rf 0.50 (SS 1); δ (CDCl3): 1.21(3H,t,J=7.1 Hz), 1.42(9H,s), 2.56 (2H,t, J=7.8 Hz), 2.72(2H,t,J=7.1 Hz), 2.88(2H,t,J=7.8 Hz), 3.32(2H,m), 3.91(2H,s), 4.09(2H,t,J=7.1 Hz), 4.53(1H, br), 6.85(1H,s), 6.86(1H,s), 6.89(1H,s), 7.17-7.21 (1H,m), 7.43-7.45(1H,m), 8.44-8.48(2H,m).

Workup

  1. temperatureunder reflux for 18 hours
  2. customevaporated under vacuum
  3. customThe residue was chromatographed on silica gel
  4. washAfter elution of some impurity
  5. customthe product fractions were obtained
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-645753d894c049a3bdd3f08b079ac94e
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

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