4-Toluenesulfonyl chloride → Methyl 4-(2-p-toluenesulphonamido-indan-5-yl)-4-oxobutyrate

HRID 1651862Notes

Reaction equation

HRID 1651862 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12](=[O:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:9]=2)[CH2:4]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12](=[O:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:9]=3)[CH2:4]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23050575Methyl 4-(2-amino-indan-5-yl)-4-oxobutyrate hydrochloride

Product 1

HCID 14071511Methyl 4-(2-p-toluenesulphonamido-indan-5-yl)-4-oxobutyrate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.0 g (21.1 mmol) of methyl 4-(2-amino-indan-5-yl)-4-oxobutyrate hydrochloride are suspended in 60 ml of chloroform and 5.0 g (25.3 mmol) of p-toluenesulphonyl chloride are added. 5.1 g (50 mmol) of triethylamine are added, with vigorous stirring, a clear solution being formed. After 20 hours at room temperature, the mixture is washed with water, the chloroform solution is evaporated and the residue is recrystallised from methanol.

Workup

  1. customa clear solution being formed
  2. washthe mixture is washed with water
  3. customthe chloroform solution is evaporated
  4. customthe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-bc74755d74a348fcb590a473b933705a
Source dataset
uspto-grants-1990_05
Patent number
US04929754

Reaction notes

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