p-Toluenesulfonic acid → Acetic acid, butoxy[[(phenylmethoxy)carbonyl]amino]-, butyl ester

HRID 1731032Notes

Reaction equation

HRID 1731032 reaction equation
[C:1](=[O:11])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:2].O.[C:13]([OH:17])(=[O:16])[CH:14]=[O:15].[C:18]1([CH3:28])[CH:23]=[CH:22]C(S(O)(=O)=O)=CC=1>CCCCCC>[CH2:4]([O:16][C:13](=[O:17])[CH:14]([O:15][CH2:28][CH2:18][CH2:23][CH3:22])[NH:2][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:11])[CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12136Benzyl carbamateHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 10497164Acetic acid, butoxy[[(phenylmethoxy)carbonyl]amino]-, butyl ester

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 3.0 g. (0.02 mol.) of benzyl carbamate, 1.8 g. (0.02 mol.) of glyoxylic acid hydrate and 0.1 g of p-toluenesulfonic acid in 50 ml. of n-butanol was slowly distilled over a one hour period. The last of the solvent was removed in vacuo to give a residue which was dissolved in hexane and filtered to remove the p-toluenesulfonic acid. The filtrate was chromatographed on alumina (Woelm, activity II) and eluted with hexane. Concentration of the eluate in vacuo and molecular distillation of the residue at 130°/0.1 mm. gave the title compound.

Workup

  1. distillationof n-butanol was slowly distilled over a one hour period
  2. customThe last of the solvent was removed in vacuo
  3. customto give a residue which
  4. filtrationfiltered
  5. customto remove the p-toluenesulfonic acid
  6. customThe filtrate was chromatographed on alumina (Woelm, activity II)
  7. washeluted with hexane
  8. distillationConcentration of the eluate in vacuo and molecular distillation of the residue at 130°/0.1 mm

Sources & evidence

ORD record
ord-fefa9666888a41ac9f923ab619c0266d
Source dataset
uspto-grants-1976_11
Patent number
US03994954

Reaction notes

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