(S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride → (S)-3-(3-Bromo-4-fluoro-phenyl)-2-[2-(2,6-difluoro-benzenesulfonylamino)-4-iodo-benzoylamino]-propionic acid methyl ester

HRID 1593884Notes

Reaction equation

HRID 1593884 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9]([NH:12][C:13]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:14]=1[C:15](O)=[O:16])(=[O:11])=[O:10].Cl.[CH3:24][O:25][C:26](=[O:38])[C@@H:27]([NH2:37])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Br:36])[CH:30]=1>>[CH3:24][O:25][C:26](=[O:38])[C@@H:27]([NH:37][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:13]=1[NH:12][S:9]([C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])(=[O:11])=[O:10])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Br:36])[CH:30]=1

Participants

3

Reactant 2

HCID 68768499(S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochlorideHCID 687736512-[[(2,6-difluorophenyl)sulfonyl]amino]-4-iodoBenzoic acid

Product 1

HCID 58999915(S)-3-(3-Bromo-4-fluoro-phenyl)-2-[2-(2,6-difluoro-benzenesulfonylamino)-4-iodo-benzoylamino]-propionic acid methyl ester

Procedure

2-(2,6-Difluoro-benzenesulfonylamino)-4-iodo-benzoic acid was coupled to (S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride as in EXAMPLE 1, Part C, to afford the title compound. HPLC: RT=10.54 min. MS (ESI+): mass calcd. for C23H17BrF3IN2O5S, 697.26; m/z found, 697/699 [M+H]+. 1H NMR (500 MHz, CDCl3): 11.37 (s, 1H), 8.11 (d, J=1.4, 1H), 7.55-7.44 (m, 1H), 7.40 (dd, J=8.3, 1.4, 1H), 7.27-7.26 (m, 1H), 7.09-7.04 (m, 2H), 7.02-6.96 (m, 3H), 6.63 (d, J=6.8, 1H), 4.98 (q, J=5.6, 1H), 3.81 (s, 3H), 3.27-3.13 (m, 2H).

Sources & evidence

ORD record
ord-1261558f7f9640b9b85fbae1b02ed22a
Source dataset
uspto-grants-2007_11
Patent number
US07297816B2

Reaction notes

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