Water → Ethyl 2(S)-phenylsulfonylamino-beta-alanine p-toluenesulfonate

HRID 1599956Notes

Reaction equation

HRID 1599956 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:4]([OH:6])=[O:5].[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1.O>CCO>[C:18]1([CH3:17])[CH:19]=[CH:20][C:21]([S:24]([OH:27])(=[O:25])=[O:26])=[CH:22][CH:23]=1.[CH2:17]([NH:1][CH2:2][C@H:3]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:4]([OH:6])=[O:5])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10752796(2S)-3-amino-2-(benzenesulfonamido)propanoic Acid

Product 1

HCID 86752459Ethyl 2(S)-phenylsulfonylamino-beta-alanine p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acid 2-1b (13.20 g, 54.1 mmol) was suspended in 500 mL EtOH, p-TsOH--H2O (11.3 g, 59 mmol) was added and the mixture was heated at reflux overnight. After distilling off the solvent, fresh EtOH was added and distilled off, then more EtOH was added and the mixture was distilled to 100 mL at which point 800 mL ether was added. After cooling to 4°, solvent was decanted from the gum which was rinsed with additional ether, and dried, providing 35-2 as a hygroscopic glass. Additional 35-2 was recovered from the solvent phase by concentration and triturating with ether (2×).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. distillationAfter distilling off the solvent, fresh EtOH
  4. additionwas added
  5. distillationdistilled off
  6. additionmore EtOH was added
  7. distillationthe mixture was distilled to 100 mL at which
  8. additionwas added
  9. temperatureAfter cooling to 4°
  10. customsolvent was decanted from the gum which
  11. washwas rinsed with additional ether
  12. customdried

Sources & evidence

ORD record
ord-6168447ff85c49f3b4eed99233186381
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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