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

HRID 2420003Notes

Reaction equation

HRID 2420003 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 1 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-toluene-sulfonic 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 1 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-toluene-sulfonic 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-0bb0e2ff6362427f89485dee3f820467
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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