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

HRID 722738Notes

Reaction equation

HRID 722738 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-d3c7151eb2394f10b5d061509ecc4bc5
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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