N-Boc-4-chloro-D-phenylalanine → 4-Chloro-D-phenylalanine methyl ester hydrochloride
Reaction equation
N1SN=C2C(S(NC3C=C(Cl)C(Cl)=CC=3C(N[C@H](CC3C=CC([Cl:30])=CC=3)C(O)=O)=O)(=O)=O)=CC=C[C:2]=12.C(OC([NH:44][C@H:45]([CH2:49][C:50]1[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=1)[C:46]([OH:48])=[O:47])=O)(C)(C)C>>[ClH:30].[CH3:2][O:48][C:46](=[O:47])[C@H:45]([NH2:44])[CH2:49][C:50]1[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=1Participants
Procedure
(R)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoylamino]-3-(4-chloro-phenyl)-propionic acid. (R)-2-(tert-Butoxycarbonylamino)-3-(4-chloro-phenyl)-propionic acid was treated as in EXAMPLE 2, Part A, to produce (R)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride as a white solid. This salt was then coupled with 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-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=10.35 min. MS (ESI−): mass calcd. for C22H15Cl3N4O5S2, 583.95; m/z found, 583/585 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.07 (s, 1H), 8.34 (d, J=7.1, 1H), 8.23 (d, J=8.8, 1H), 7.84 (s, 1H), 7.74-7.70 (m, 1H), 7.30-7.26 (m, 2H), 7.24 (s, 1H), 7.07 (d, J=8.3, 2H), 6.38 (d, J=7.4, 1H), 5.00-4.97 (m, 1H), 3.30 (dd, J=14.1, 5.9, 1H), 3.21 (dd, J=14.1, 5.9, 1H).
Sources & evidence
- ORD record
- ord-897b41202d5e4fa1945bba3db6aad1a9
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07297816B2
Reaction notes
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