L-Glutamic acid dibenzyl ester tosylate → 3-(2,3-dimethoxy-5-methylbenzoquinon-6-yl)-propionyl-L-glutamic acid

HRID 370395Notes

Reaction equation

HRID 370395 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:27])[C:5]([CH2:13][CH2:14][C:15]([O:17]C2C=CC([N+]([O-])=O)=CC=2)=O)=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:39][C@H:40]([C:53]([O:55]CC1C=CC=CC=1)=[O:54])[CH2:41][CH2:42][C:43]([O:45]CC1C=CC=CC=1)=[O:44]>>[CH3:1][O:2][C:3]1[C:4](=[O:27])[C:5]([CH2:13][CH2:14][C:15]([NH:39][C@H:40]([C:53]([OH:55])=[O:54])[CH2:41][CH2:42][C:43]([OH:45])=[O:44])=[O:17])=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 13233366L-Glutamic acid dibenzyl ester tosylateHCID 14180316p-Nitropenyl 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionate

Product 1

HCID 135185063-(2,3-dimethoxy-5-methylbenzoquinon-6-yl)-propionyl-L-glutamic acidYield 25.6%

Procedure

Using p-nitrophenyl 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionate (187 mg, 0.5 mmol) and dibenzyl L-glutamate p-toluenesulfonate (250 mg, 0.5 mmol) and following the procedure of Example 4, there was obtained 3-(2,3-dimethoxy-5-methylbenzoquinon-6-yl)propionyl-L-glutamic acid (49 mg).

Sources & evidence

ORD record
ord-554ea538650c4f3a9d507e4384cee21c
Source dataset
uspto-grants-1985_07
Patent number
US04526719

Reaction notes

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