2-Methylbenzenesulfonic acid → Acetic acid, butoxy[[(phenylmethoxy)carbonyl]amino]-, butyl ester

HRID 1973476Notes

Reaction equation

HRID 1973476 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].C1(C)C(S(O)(=O)=O)=[CH:20][CH:21]=[CH:22][CH:23]=1>CCCCCC>[CH2:4]([O:16][C:13](=[O:17])[CH:14]([O:15][CH2:23][CH2:22][CH2:21][CH3:20])[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 69252-Methylbenzenesulfonic 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 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-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 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-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-f48cc3f1ca6c491bbc56af2a071fc0c4
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

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