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

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

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.