HCID 68772132, compound → HCID 58999922, compound

HRID 2265271Notes

Reaction equation

HRID 2265271 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)[CH:19]=[CH:18][C:14]=1[C:15](O)=[O:16])(=[O:11])=[O:10].[ClH:23].C[O:25][C:26](=[O:38])[C@H:27]([NH2:37])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1>>[Cl:23][C:20]1[CH:19]=[CH:18][C:14]([C:15]([NH:37][C@H:27]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[C:26]([OH:25])=[O:38])=[O:16])=[C:13]([NH:12][S:9]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[F:8])(=[O:11])=[O:10])[CH:21]=1

Participants

3

Reactant 2

HCID 68772132HCID 68772132, compoundHCID 687736512-[[(2,6-difluorophenyl)sulfonyl]amino]-4-iodoBenzoic acid

Product 1

HCID 58999922HCID 58999922, compound

Procedure

2-(2,6-Difluoro-benzenesulfonylamino)-4-iodo-benzoic acid was coupled to (R)-2-amino-3-(3,4-dichloro-phenyl)-propionic acid methyl ester hydrochloride as in EXAMPLE 1, Part C. The resulting methyl ester was hydrolyzed as in EXAMPLE 2, Part E, to afford the title compound. HPLC: RT=11.00 min. MS (ESI−): mass calcd. for C22H15Cl3F2N2O5S, 563.79; m/z found, 561/563 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.45 (s, 1H), 7.75 (d, J=1.9, 1H), 7.53-7.44 (m, 1H), 7.36 (d, J=8.2, 1H), 7.31-7.25 (m, 2H), 7.06-6.96 (m, 4H), 6.61 (d, J=6.9, 1H), 5.03 (d, J=5.6, 1H), 3.38-3.17 (m, 2H).

Sources & evidence

ORD record
ord-c8aacf84d1c8473db4fc49e6022ab6ee
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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