L-Methionine → 4-Nitro-2-phenylbenzoyl-(S)-leucine methyl ester

HRID 1739154Notes

Reaction equation

HRID 1739154 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][CH:14]=2)[CH:5]=1)([O-:3])=[O:2].Cl.[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH2:24].N[C@H](C(O)=O)CCSC>>[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[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][CH:14]=1

Participants

4

Reactant 3

HCID 6137L-MethionineHCID 2723695Leucine methyl ester hydrochlorideHCID 106578414-Nitro-2-phenylbenzoic acid

Product 1

HCID 106428984-Nitro-2-phenylbenzoyl-(S)-leucine methyl ester

Procedure

This compound was prepared through the coupling of 4-nitro-2-phenylbenzoic acid with (L)-leucine methyl ester hydrochloride as for the preparation of the methionine derivative (see Example 26, section A). 1H NMR (CDCl3) δ 8.24-8.26 (m, 2H), 7.86 (d, 8.7 Hz, 1H), 7.41-7.46 (m, 5H), 5.71 (d, 7.4 Hz, 1H), 4.57 (ddd, 1H), 3.67 (s, 3H), 1.37-1.46 (m, 1H), 1.08-1.25 (m, 2H), 0.78 (dd, 6H).

Sources & evidence

ORD record
ord-fea62552f89f4c50a1d5fb9b178d0509
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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