methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride → HCID 11534410, compound

HRID 1593851Notes

Reaction equation

HRID 1593851 reaction equation
Cl.C[O:3][C:4](=[O:14])[C@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[S:23]([NH:26][C:27]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:28]=1[C:29](O)=[O:30])(=[O:25])=[O:24]>>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[S:23]([NH:26][C:27]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:28]=1[C:29]([NH:13][C@H:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:3])=[O:14])=[O:30])(=[O:25])=[O:24]

Participants

3

Reactant 2

HCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochlorideHCID 687736512-[[(2,6-difluorophenyl)sulfonyl]amino]-4-iodoBenzoic acid

Product 1

HCID 11534410HCID 11534410, compound

Procedure

(R)-2-[2-(2.6-Difluoro-benzenesulfonylamino)-4-iodo-benzoylamino]-3-phenyl-propionic acid. (R)-2-(tert-Butoxycarbonylamino)-3-phenyl-propionic acid was treated as in EXAMPLE 2, Part A, to produce (R)-2-amino-3-phenyl-propionic acid methyl ester hydrochloride as a white solid. This ester was coupled with 2-(2,6-difluoro-benzenesulfonylamino)-4-iodo-benzoic acid 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=9.27 min. MS (ESI−): mass calcd. for C22H17F2IN2O5S, 585.99; m/z found, 584/586[M−H]−. 1H NMR (500 MHz, CDCl3): 11.32 (s, 1H), 8.11 (s, 1H), 7.50-7.46 (m, 1H), 7.38-7.28 (m, 4H), 7.16-7.15 (m, 2H), 7.00-6.96 (m, 3H), 6.51 (d, J=7.6, 1H), 5.07-5.03 (m, 1H), 3.34 (dd, J=14.0, 5.6, 1H), 3.25 (dd, J=14.3, 5.3, 1H).

Sources & evidence

ORD record
ord-04edf4429074461fbeb7e8e778fe18a4
Source dataset
uspto-grants-2007_11
Patent number
US07297816B2

Reaction notes

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