methyl (2S)-2-amino-4-(methylsulfanyl)butanoate → [4-Nitro-2-(2-methylphenyl)benzoyl]methionine methyl ester
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:5]=1)([O-:3])=[O:2].[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH2:26][S:27][CH3:28])[NH2:24].Cl.C(N=C=NCCCN(C)C)C.ON1C(=O)C2C=CC=CC=2N=N1>>[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH2:26][S:27][CH3:28])[NH:24][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]Participants
Reactant 4
Product 1
Procedure
4-Nitro-2-(2-methylphenyl)benzoic acid (2.31 g, 9 mmol), prepared as in Example 178B, was coupled with L-methionine methyl ester (1.0 eq) in the presence of ethyl dimethylaminopropyl carbodiimide hydrochloride (EDCI, 1.0 eq) and 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (HOBT, 1.0 eq) to give [4-nitro-2-(2-methylphenyl)benzoyl]methionine methyl ester as a pale yellow oil (3.54 g, 98% yield); 1H NMR showed diastereomers due to restricted carbon-carbon bond rotation; 1H NMR (CDCl3) δ 8.26-8.30 (d, J=8.5 Hz, 1H), 8.10 (s, 1H), 8.03-8.09 (m, 1H), 7.27-7.42 (m, 3.5H), 7.18 (d, J=7.4 Hz, 0.5H), 6.03 (br, 1H, amide), 4.59-4.67 (m, 1H), 3.67 (s, 3H), 2.23 (s, 1.5H, PhCH3), 2.06 (s, 1.5H, PhCH3), 1.98-2.03 (m, 5H), 1.81-1.93 (m, 1H), 1.59-1.69 (m, 1H).
Sources & evidence
- ORD record
- ord-851304cf787b416f98bce15c5ebd0961
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06693123B2
Reaction notes
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