Acetic Acid → 3-(4-thiazolyl)-L-alanine diphenylmethylester p-toluenesulfonate

HRID 429756Notes

Reaction equation

HRID 429756 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[S:12]1[CH:16]=[C:15]([CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])[N:14]=[CH:13]1.C1COCC1.[C:28]1([C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N+]=[N-])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)C>C(O)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[C:28]1([CH:34]([O:21][C:20](=[O:22])[C@H:18]([CH2:17][C:15]2[N:14]=[CH:13][S:12][CH:16]=2)[NH2:19])[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 612301,1'-(Diazomethylene)bis(benzene)2×HCID 867576003-(4-thiazolyl)-L-alanine p-toluenesulfonate

Product 1

HCID 207060783-(4-thiazolyl)-L-alanine diphenylmethylester p-toluenesulfonateYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 38.85 g of the compound (43) (112.8 mmol) in ethanol (200 ml)-THF (600 ml) was added diphenyldiazomethane (39 g, 201 mmol) little, by little over 30 min. at room temperature with stirring. After the reaction mixture was stirred for 1 h at room temperature, to the mixture was added diphenyldiazomethane (10 g, 51.5 mmol) and the resulting mixture was stirred for 1 h. To the reaction mixture was added acetic acid (0.1 ml) for quenching the excess reagent and the mixture was concentrated in vacuo. The residue (92 g) was crystallized by adding ether (1 L) to give 49.05 g (96.1%) of the compound (44).

Workup

  1. stirringAfter the reaction mixture was stirred for 1 h at room temperature, to the mixture
  2. stirringthe resulting mixture was stirred for 1 h
  3. customfor quenching the excess reagent
  4. concentrationthe mixture was concentrated in vacuo
  5. customThe residue (92 g) was crystallized
  6. additionby adding ether (1 L)

Sources & evidence

ORD record
ord-c8878d1f1d7446cd84b6489225952cd9
Source dataset
uspto-grants-2001_11
Patent number
US06319902B1

Reaction notes

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