2-Benzothiazolesulfonyl chloride → N-[2-[(2-Benzothiazolylsulfonyl)amino]ethyl]-L-alanine ethyl ester

HRID 857542Notes

Reaction equation

HRID 857542 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:13])[C@H:7]([CH3:12])[NH:8][CH2:9][CH2:10][NH2:11])[CH3:4].[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[S:23](Cl)(=[O:25])=[O:24]>>[CH2:3]([O:5][C:6](=[O:13])[C@H:7]([CH3:12])[NH:8][CH2:9][CH2:10][NH:11][S:23]([C:15]1[S:14][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=1)(=[O:24])=[O:25])[CH3:4]

Participants

3

Reactant 2

HCID 97946612-Benzothiazolesulfonyl chlorideHCID 23404547N-(2-Aminoethyl)-alanine ethylester 2HCl

Product 1

HCID 68520685N-[2-[(2-Benzothiazolylsulfonyl)amino]ethyl]-L-alanine ethyl ester

Procedure

N-(2-Aminoethyl)-alanine ethylester 2HCl, prepared as described by Puschl (A. Puschl et al., Tetrahedron, 1998, 39, 4707.), was reacted with benzothiazole-2-sulfonyl chloride as per the procedure of Example 1 to give the title compound. 1H NMR (500 MHz; DMSO-d6) δ 8.27 (d, 1H), 8.18 (d, 1H), 7.69˜7.62 (m, 2H), 4.01 (q, 2H), 3.17 (q, 1H), 3.13 (t, 2H), 2.61 (m, 1H), 2.49 (m, 1H), 1.13 (t, 3H), 1.06 (d, 3H).

Sources & evidence

ORD record
ord-5c88985a774a49ab80bb95e2dcc13554
Source dataset
uspto-grants-2006_12
Patent number
US07145006B2

Reaction notes

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