HCID 68769642, compound → (2S,3R)-3-(3,4-Dichloro-phenyl)-2-[2-(2,6-difluoro-benzenesulfonylamino)-4-iodo-benzoylamino]-butyric acid methyl ester

HRID 2265267Notes

Reaction equation

HRID 2265267 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]([OH:17])=O)(=[O:11])=[O:10].[CH3:23][O:24][C:25](=[O:38])[C@@H:26]([NH2:37])[C@@H:27]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)[CH3:28]>>[CH3:23][O:24][C:25](=[O:38])[C@@H:26]([NH:37][C:15](=[O:17])[C:14]1[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:13]=1[NH:12][S:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])(=[O:11])=[O:10])[C@@H:27]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)[CH3:28]

Participants

3

Reactant 2

HCID 68769642HCID 68769642, compoundHCID 687736512-[[(2,6-difluorophenyl)sulfonyl]amino]-4-iodoBenzoic acid

Product 1

HCID 58999889(2S,3R)-3-(3,4-Dichloro-phenyl)-2-[2-(2,6-difluoro-benzenesulfonylamino)-4-iodo-benzoylamino]-butyric acid methyl ester

Procedure

2-(2,6-Difluoro-benzenesulfonylamino)-4-iodo-benzoic acid was coupled to (2S,3R)-2-amino-3-(3,4-dichloro-phenyl)-butyric acid methyl ester as in EXAMPLE 1, Part C, to afford the title compound. HPLC: RT=12.39 min. MS (ESI+): mass calcd. for C24H19Cl2F2IN2O5S, 683.29; m/z found, 683/685 [M+H]+. 1H NMR (400 MHz, CDCl3): 11.29 (s, 1H), 8.11 (d, J=1.6, 1H), 7.52-7.47 (m, 1H), 7.42 (dd, J=8.3, 1.6, 1H), 7.37 (d, J=13.9, 1H), 7.24 (d, J=2.1, 2H), 7.11 (d, J=8.3, 1H), 7.02-6.98 (m, 3H), 6.65 (d, J=8.3, 1H), 4.95-4.91 (m, 1H), 3.26 (s, 3H), 3.31 (quin, J=7.2, 1H), 1.43 (d, J=7.2, 3H).

Sources & evidence

ORD record
ord-b18a53aa8d2e4d3fb0aa6e558dfc7fe1
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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