4-Chloro-5-methoxy-benzothiazole-2-sulfonyl chloride → [2-(4-Chloro-5-methoxy benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester

HRID 857541Notes

Reaction equation

HRID 857541 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH2:11])[CH3:4].[Cl:13][C:14]1[C:19]2[N:20]=[C:21]([S:23](Cl)(=[O:25])=[O:24])[S:22][C:18]=2[CH:17]=[CH:16][C:15]=1[O:27][CH3:28]>>[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][S:23]([C:21]1[S:22][C:18]2[CH:17]=[CH:16][C:15]([O:27][CH3:28])=[C:14]([Cl:13])[C:19]=2[N:20]=1)(=[O:25])=[O:24])[CH3:4]

Participants

3

Reactant 2

HCID 218684454-Chloro-5-methoxy-benzothiazole-2-sulfonyl chlorideHCID 74889816N-beta-Aminoethyl-gly-oet 2hcl

Product 1

HCID 21868411[2-(4-Chloro-5-methoxy benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl esterYield 89%

Procedure

The title compound (726 mg, 89%) was synthesized by the reaction of N-(2-aminoethyl)-glycine ethyl ester 2HCl (398 mg, 2.0 mmol) with 4-chloro-5-methoxy-benzothiazole-2-sulfonyl chloride (596 mg, 2.0 mmol) as per the procedure of Example 1. 1H NMR (500 MHz; DMSO-d6) δ 8.18 (d, 1H), 7.57 (d, 1H), 4.00 (q, 2H), 3.97 (s, 3H), 3.22 (s, 2H), 3.14 (t, 2H), 2.62 (t, 2H), 1.13 (t, 3H).

Sources & evidence

ORD record
ord-5fa36e8b1d4e45c285cdff24ea48767a
Source dataset
uspto-grants-2006_12
Patent number
US07145006B2

Reaction notes

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