O-benzyl-L-tyrosine → 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionyl-L-tyrosine

HRID 580229Notes

Reaction equation

HRID 580229 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].C([O:35][C:36]1[CH:47]=[CH:46][C:39]([CH2:40][C@@H:41]([C:43]([OH:45])=[O:44])[NH2:42])=[CH:38][CH:37]=1)C1C=CC=CC=1>>[CH3:1][O:2][C:3]1[C:4](=[O:27])[C:5]([CH2:13][CH2:14][C:15]([NH:42][C@H:41]([C:43]([OH:45])=[O:44])[CH2:40][C:39]2[CH:38]=[CH:37][C:36]([OH:35])=[CH:47][CH:46]=2)=[O:17])=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 725701O-benzyl-L-tyrosineHCID 14180316p-Nitropenyl 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionate

Product 1

HCID 135185083-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionyl-L-tyrosineYield 20.6%

Procedure

Using p-nitrophenyl 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionate (187 mg, 0.5 mmol) and O-benzyl-L-tyrosine (136 mg, 0.5 mmol) and following the procedure of Example 4, there was obtained 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionyl-L-tyrosine (43 mg), melting at 170° C.

Sources & evidence

ORD record
ord-7c88d446e82e4c9e9988b1b30bb8afaa
Source dataset
uspto-grants-1988_06
Patent number
US04751303

Reaction notes

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