N-Acetyl-L-leucine → N-acetyl-L-leucinate

HRID 1462973Notes

Reaction equation

HRID 1462973 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)=[CH:4][C:3]=1[O:23][CH3:24].[C:25]([NH:28][C@H:29]([C:34]([OH:36])=[O:35])[CH2:30][CH:31]([CH3:33])[CH3:32])(=[O:27])[CH3:26]>CO>[C:25]([NH:28][C@H:29]([C:34]([O-:36])=[O:35])[CH2:30][CH:31]([CH3:32])[CH3:33])(=[O:27])[CH3:26].[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)=[CH:4][C:3]=1[O:23][CH3:24]

Participants

5

Reactant 2

HCID 70912N-Acetyl-L-leucineHCID 11186519(-)-7-Hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Product 2

HCID 6928495N-acetyl-L-leucinateHCID 11186519(-)-7-Hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

18.9 g. (57.4 mmol) (±)-7-Hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline are dissolved at 60° C. in 70 ml. methanol and mixed with a solution of 9.94 g. (57.4 mmol) N-acetyl-L-leucine in 50 ml. methanol, also heated to 60° C. The solution obtained is concentrated by evaporating in a vacuum. After the addition of isopropanol/diethyl ether and recrystallisation from the same solvent mixture, there is obtained the N-acetyl-L-leucinate of (-)-7-hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline; m.p. 179°-186° C.

Workup

  1. customThe solution obtained
  2. concentrationis concentrated
  3. customby evaporating in a vacuum
  4. additionAfter the addition of isopropanol/diethyl ether and recrystallisation from the same solvent mixture

Sources & evidence

ORD record
ord-63474b94aa8e4f1e947d66ac3f62d6c7
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

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