2,4-Dichloro-L-phenylalanine → HCID 68768460, compound
Reaction equation
Br[C:2]1C=CC(C(NC(CC2C=CC([Cl:20])=CC=2Cl)C(O)=O)=O)=C(NS(C2C(F)=CC=CC=2F)(=O)=O)C=1.[NH2:36][C@@H:37]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=1[Cl:49])[C:38]([OH:40])=[O:39]>>[ClH:20].[CH3:2][O:39][C:38](=[O:40])[C@@H:37]([NH2:36])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=1[Cl:49]Participants
Procedure
2-[4-Bromo-2-(2,6-difluoro-benzenesulfonylamino)-benzoylamino]-3-(2,4-dichloro-phenyl)-propionic acid. (S)-2-Amino-3-(2,4-dichloro-phenyl)-propionic acid was treated as in EXAMPLE 2, Part A, to produce (S)-2-amino-3-(2,4-dichloro-phenyl)-propionic acid methyl ester hydrochloride as a white solid. This ester was coupled with 4-bromo-2-(2,6-difluoro-benzenesulfonylamino)-benzoic acid as in EXAMPLE 1, Part C. The resulting methyl ester was hydrolyzed as in EXAMPLE 2, Part E, to afford title compound. HPLC: RT=10.26 min. MS (ESI−): mass calcd. for C22H15BrCl2F2N2O5S, 608.2; m/z found, 607 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.36 (s, 1H), 7.87 (d, J=1.8, 1H), 7.52-7.44 (m, 1H), 7.39 (d, J=1.6, 1H), 7.27-7.25 (m, 1H), 7.25-7.22 (m, 1H), 7.18-7.15 (m, 1H), 6.97 (t, J=8.7, 2H), 6.79 (d, J=7.7, 1H), 5.05-5.00 (m, 1H), 3.50 (dd, J=14.2, 5.5, 1H), 3.29 (dd, J=14.2, 8.1, 1H).
Sources & evidence
- ORD record
- ord-ebd5157e450b46d1944580f734b8c9e2
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07297816B2
Reaction notes
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