p-Toluenesulfonic acid monohydrate → 3-(4-thiazolyl)-L-alanine p-toluenesulfonate

HRID 429755Notes

Reaction equation

HRID 429755 reaction equation
C(OC([NH:8][C@H:9]([C:16]([OH:18])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=O)(C)(C)C.O.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([OH:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1>FC(F)(F)C(O)=O>[C:20]1([CH3:30])[CH:21]=[CH:22][C:23]([S:26]([OH:29])(=[O:27])=[O:28])=[CH:24][CH:25]=1.[S:14]1[CH:15]=[C:11]([CH2:10][C@@H:9]([C:16]([OH:18])=[O:17])[NH2:8])[N:12]=[CH:13]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 2734486(S)-2-((tert-Butoxycarbonyl)amino)-3-(thiazol-4-yl)propanoic acid

Product 1

HCID 867576003-(4-thiazolyl)-L-alanine p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (80 ml) was added to N-(tert-butoxycarbonyl)-3-(4-thiazolyl)-L-alanine (42, 21.79 g, 80 mmol) which was synthesized in accordance with the method described in the literature (Synth. Commun., 20, 3507 (1990)) and the resulting mixture was stirred for 2 h under ice-cooling, Subsequently, to the mixture was added p-toluenesulfonic acid hydrate (15.22 g, 80 mmol) and the resulting mixture was stirred for 30 min. at room temperature. The reaction mixture was concentrated in vacuo. To the residue was added water and methanol, and excess trifluoroacetic acid was removed by concentrating in vacuo. To the residue was added diethyl ether and the precipitation which appeared was filtered off to give 29.8 g (quantitative) of the compound (43).

Workup

  1. customwas synthesized in accordance with the method
  2. temperaturecooling
  3. stirringthe resulting mixture was stirred for 30 min. at room temperature
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additionTo the residue was added water and methanol, and excess trifluoroacetic acid
  6. customwas removed
  7. concentrationby concentrating in vacuo
  8. additionTo the residue was added diethyl ether
  9. customthe precipitation which
  10. filtrationappeared was filtered off

Sources & evidence

ORD record
ord-4a449dc237e145198248e8873c09b7ac
Source dataset
uspto-grants-2001_11
Patent number
US06319902B1

Reaction notes

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