2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acid → (S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid methyl ester

HRID 2265280Notes

Reaction equation

HRID 2265280 reaction equation
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Br:23])[CH:20]=[CH:19][C:15]=3[C:16](O)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.Cl.[CH3:25][O:26][C:27](=[O:39])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)[NH2:29]>>[CH3:25][O:26][C:27](=[O:39])[C@@H:28]([NH:29][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:21]([Br:23])=[CH:22][C:14]=1[NH:13][S:10]([C:6]1[C:3]2=[N:4][S:5][N:1]=[C:2]2[CH:9]=[CH:8][CH:7]=1)(=[O:12])=[O:11])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1

Participants

3

Reactant 2

HCID 160907442-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acidHCID 46735197H-Phe(3,4-DiCl)-OMe.HCl

Product 1

HCID 68771622(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid methyl esterYield 95%

Procedure

The title compound (61 mg, 95%) was prepared from 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acid and (S)-3,4-dichlorophenylalanine methyl ester hydrochloride as in Example 1, Part C. 1H NMR (400 MHz, CDCl3): 11.43 (br s, 1H), 8.38 (dd, J=7.0, 1.0, 1H), 8.23 (dd, J=8.8, 1.0, 1H), 7.90 (t, J=1.0, 1H), 7.73 (dd, J=8.8, 7.0, 1H), 7.35 (d, J=8.2, 1H), 7.14 (d, J=2.0, 1H), 7.11 (d, J=1.0, 2H), 6.89 (dd, J=8.2, 2.1, 1H), 6.48 (br d, J=7.1, 1H), 5.00-4.92 (m, 1H), 3.82 (s, 3H), 3.22 (dd, J=14.0, 5.8, 1H), 3.16 (dd, J=14.0, 5.1, 1H).

Sources & evidence

ORD record
ord-01b5b26cf7fc42ed83a90c2a5a0e667f
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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