Benzylamine → HCID 86737477, compound

HRID 1413402Notes

Reaction equation

HRID 1413402 reaction equation
C(N)C1C=CC=CC=1.[CH2:9]([N:12](C(OCC1C=CC=CC=1)=O)[CH2:13][C:14]([NH:16][C@H:17]([C:19]([NH:21][C@H:22]([C:24]([NH:26][C@H:27]([P:29](=[O:32])([OH:31])[OH:30])[CH3:28])=[O:25])[CH3:23])=[O:20])[CH3:18])=[O:15])[CH:10]=[CH2:11]>O.C(O)C>[CH2:9]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:19]([NH:21][C@H:22]([C:24]([NH:26][C@H:27]([P:29](=[O:30])([OH:32])[OH:31])[CH3:28])=[O:25])[CH3:23])=[O:20])[CH3:18])=[O:15])[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 54234971HCID 54234971, compound

Product 1

HCID 86737477HCID 86737477, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

In a manner analogous to that described in Example 1(B)(ii), from the monobenzylamine salt of (1R)-1-[(N-allyl-N-benzyloxycarbonyl-glycyl-L-alanyl-L-alanyl)amino]-ethylphosphonic acid, but using water/ethanol (1:1) for the ion-exchange step to generate the free acid, there was obtained, after hydrogenolysis of the N-benzyloxycarbonyl group in the usual way but with concomitant reduction of the allyl group to the n-propyl group, the crude product in the form of a gel. Crystallisation from water/ethanol gave (1R)-1-[N-(n-propyl)-glycyl-L-alanyl-L-alanylamino]-ethylphosphonic acid of melting point 263°-264° C. (decomposition); [α]D20 =-110°; [α]36520 =-392° (c=1% in water).

Workup

  1. customthere was obtained
  2. customCrystallisation from water/ethanol

Sources & evidence

ORD record
ord-0323716db8e2486eafa3c97a873c635c
Source dataset
uspto-grants-1981_02
Patent number
US04250085

Reaction notes

Loading…