3-Chloropropanesulphonyl chloride → methyl (S)-4-[1-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)ethyl]benzoate

Reaction equation

[NH2:1][C@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3].Cl[CH2:15][CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19]>>[O:19]=[S:18]1(=[O:20])[CH2:17][CH2:16][CH2:15][N:1]1[C@H:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3]

Participants

Reactant 2

HCID 154103-Chloropropanesulphonyl chloride

HCID 17751895Methyl 4-((1S)-1-aminoethyl)benzoate

Product 1

HCID 71261170methyl (S)-4-[1-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)ethyl]benzoate

Procedure

Using methyl (S)-4-(1-aminoethyl)benzoate (0.61 g) and 3-chloropropane-1-sulfonyl chloride (0.54 mL) and by the reaction and treatment in the same manner as in Preparation Example 17, the title compound (0.90 g) was obtained.

Workup

customby the reaction and treatment in the same manner
customas in Preparation Example 17

Sources & evidence

ORD record: ord-70fc857922274c519bb0849776f49c26
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816079B2

Reaction notes

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