L-Alanine → 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionyl-L-alanine

HRID 580225Notes

Reaction equation

HRID 580225 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].[NH2:28][C@H:29]([C:31]([OH:33])=[O:32])[CH3:30].C(N1CCOCC1)C>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4](=[O:27])[C:5]([CH2:13][CH2:14][C:15]([NH:28][C@H:29]([C:31]([OH:33])=[O:32])[CH3:30])=[O:17])=[C:6]([CH3:12])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 7525EthylmorpholineHCID 14180316p-Nitropenyl 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionate

Product 1

HCID 135184993-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionyl-L-alanineYield 14.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of p-nitrophenyl 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionate (187 mg, 0.5 mmol) and L-alanine (45 mg, 0.5 mmol) in N,N-dimethylformamide (5 ml) was added N-ethylmorpholine (128 μl, 1.0 mmol). The mixture was stirred at room temperature for 2 days. After completion of the reaction, the solvent was distilled off and the residue was chromatographed on a Sephadex LH20 column under the same conditions as above. The eluate was evaporated to give 3-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)propionyl-L-alanine (23 mg).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe residue was chromatographed on a Sephadex LH20 column under the same conditions as above
  4. customThe eluate was evaporated

Sources & evidence

ORD record
ord-ac4adb9e47854603bdaf3b7604097252
Source dataset
uspto-grants-1988_06
Patent number
US04751303

Reaction notes

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