Ethanol → 5-Hydroxy-L-tryptophyl-L-aspartic acid--water (1/3)

HRID 462933Notes

Reaction equation

HRID 462933 reaction equation
C([O:8]C([NH:11][C@H:12]([C:34]([NH:36][C@H:37]([C:44]([O:46]CC)=[O:45])[CH2:38][C:39]([O:41]CC)=[O:40])=[O:35])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23]C(OCC3C=CC=CC=3)=O)[CH:21]=2)[NH:16][CH:15]=1)=O)C1C=CC=CC=1.C([OH:51])C>C(O)(=O)C.[Pd]>[OH2:8].[OH2:51].[OH2:8].[OH:23][C:20]1[CH:21]=[C:22]2[C:17]([NH:16][CH:15]=[C:14]2[CH2:13][C@@H:12]([C:34]([NH:36][C@H:37]([C:44]([OH:46])=[O:45])[CH2:38][C:39]([OH:41])=[O:40])=[O:35])[NH2:11])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 10153468HCID 10153468, compound

Product 1

HCID 684908235-Hydroxy-L-tryptophyl-L-aspartic acid--water (1/3)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

32 g (0.05 mol) of the derivative obtained above according to (a) are dissolved in 600 ml of acetic acid and 600 ml of ethanol and the solution is hydrogenated at atmospheric pressure in the presence of 3 g of 5% palladium-on-charcoal. When the absorption of hydrogen has ended, the mixture is filtered, the filtrate is evaporated, the residue is made into a paste again with ether and the product is recrystallized from water. This gaves 86% of the trihydrate of the title derivative of m.p. 190° C. and [α]D =+12.40° (C=1, 0.1N NH4OH). TLC of the product on a Kieselgel plate in the system isopropanol 2/ethyl acetate 2/water 1/acetic acid 0.1 gives a single spot of Rf=0.65.

Workup

  1. custom32 g (0.05 mol) of the derivative obtained
  2. customWhen the absorption of hydrogen
  3. filtrationthe mixture is filtered
  4. customthe filtrate is evaporated
  5. customthe product is recrystallized from water
  6. customderivative of m.p. 190° C. and [α]D =+12.40° (C=1, 0.1N NH4OH)
  7. customTLC of the product on a Kieselgel plate in the system isopropanol 2/ethyl acetate 2/water 1/acetic acid 0.1 gives a single spot of Rf=0.65

Sources & evidence

ORD record
ord-1f9e86fc4da045adb8372c0fc1356963
Source dataset
uspto-grants-1985_05
Patent number
US04518587

Reaction notes

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