p-Toluenesulfonic acid → 3-Allyloxycarbonylamino-4,4-diethoxy-butyric acid tert-butyl ester

HRID 891215Notes

Reaction equation

HRID 891215 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH:8]([NH:11][C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH:9]=[O:10])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])[O:20][CH2:21][CH3:22].[C:25]1(C)C=CC(S(O)(=O)=O)=C[CH:26]=1>C(O)C>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH:8]([NH:11][C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH:9]([O:20][CH2:21][CH3:22])[O:10][CH2:25][CH3:26])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 184657153-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl esterHCID 53630039Ethylorthoformate

Product 1

HCID 235987123-Allyloxycarbonylamino-4,4-diethoxy-butyric acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester, 102, (13.3 g, 51.7 mmol) in anhydrous ethanol (75 mL) is added ethyl orthoformate (45 mL, 0.270 mol), p-toluenesulfonic acid (0.15 g, cat.) and 4 Å molecular sieves (10 g, kiln dried) under N2. After the consumption of starting material, the sieves are removed by filtration and the solvent removed in vacuo to provide the desired compound as a clear oil which is used directly without further purification. MS (ESI): m/e=332.21 (M+H).

Workup

  1. customAfter the consumption of starting material
  2. customthe sieves are removed by filtration
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3f60a1ecbef64dee8d10143acfbb30e3
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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