1,4-Dioxane hydrochloride → O-benzyl-L-tyrosine

HRID 330427Notes

Reaction equation

HRID 330427 reaction equation
C1(N[C:8](=[O:35])[C@H:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31]C=3)=O)=[CH:21][CH:20]=2)[NH:10]C(OC(C)(C)C)=O)CCCCC1.Cl.[O:37]1CCOCC1>CCCCCC>[CH2:26]([O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C@@H:9]([C:8]([OH:35])=[O:37])[NH2:10])=[CH:24][CH:23]=1)[C:27]1[CH:29]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 70070014N-(t-butyloxycarbonyl)-4-phenacyloxy-L-phenylalanine cyclohexylamide

Product 1

HCID 725701O-benzyl-L-tyrosine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To the above compound (II) (1.0 g) was added under ice-cooling 4N-hydrogen chloride/dioxane solution (4.5 ml) and the mixture was stirred at room temperature for 30 minutes. Hexane (30 ml) was added to this solution and the precipitated crystalline substance was collected by filtration, washed with ether and then dried under reduced pressure to give quantitatively 4-benzyloxy-L-phenylalanine 4-cis/trans-methylcyclohexylamide hydrochloride (III). On the other hand, triethylamine (0.6 ml) was added to a solution of trans-4-(t-butyloxycarbonyl)aminomethylcyclohexylcarboxylic acid (0.62 g) dissolved in dry tetrahydrofuran (30 ml) and ethyl chlorocarbonate (0.25 g) was added under ice-cooling, followed by stirring for 30 minutes. To this solution were added the above compound (III) (0.73 g) and triethylamine (1 ml), and the mixture was stirred at room temperature for 3 hours. After evaporation of the solvent, the residue was extracted with ethyl acetate, washed with water and dried to give 0.2 g of N-[trans-4-(t-butyloxycarbonyl)aminomethylcyclohexylcarbonyl]-4-benzyloxyl-L-phenylalanine 4-cis/trans-methylcyclohexylamide (IV). To the above compound (IV) (0.2 g) was added under ice-cooling 4N-hydrogen chloride/dioxane solution (0.5 ml) and the mixture was stirred at room temperature for 30 minutes. Hexane (20 ml) was added to this solution and the precipitated crystalline substance was collected by filtration, washed with ether and then dried under a reduced pressure to give 0.1 g of N-(trans-4-aminomethylcyclohexylcarbonyl)-4-benzyloxy-L-phenylalanine 4-cis/trans-methylcyclohexylamide hydrochloride.

Workup

  1. filtrationthe precipitated crystalline substance was collected by filtration
  2. washwashed with ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-1fbbeb6d5b0e46e1856aead20ad39490
Source dataset
uspto-grants-1990_01
Patent number
US04895842

Reaction notes

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