3,5-Dibromosalicylaldehyde → N-(3,5-dibromosalicylidene)-(S)-valine

HRID 1032893Notes

Reaction equation

HRID 1032893 reaction equation
C([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])(OCC1C=CC=CC=1)=O.[Br:19][C:20]1[CH:27]=[C:26]([Br:28])[CH:25]=[C:22]([CH:23]=O)[C:21]=1[OH:29]>>[Br:19][C:20]1[CH:27]=[C:26]([Br:28])[CH:25]=[C:22]([CH:23]=[N:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])[C:21]=1[OH:29]

Participants

3

Reactant 2

HCID 70243,5-DibromosalicylaldehydeHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 135430615N-(3,5-dibromosalicylidene)-(S)-valineYield 68%

Procedure

The desired product was prepared in the same manner as the latter half procedure of Reference Example 1. That is, carbobenzoxy-(S)-valine piperizide (0.32 g, 1 mmol) was hydrogenated and then condensed with 3,5-dibromosalicylaldehyde (0.42 g, 1.5 mmol) to obtain 0.30 g (68%) of the desired N-(3,5-dibromosalicylidene)-(S)-valine piperizide, which was further recrystallized from methanol. m.p. 143.2°-145.4° C. [α]26D +50.1° (c 0.97, CHCl3)

Workup

  1. customThe desired product was prepared in the same manner as the latter half procedure of Reference Example 1

Sources & evidence

ORD record
ord-d9dc418b19824ee49b08f546e140c3a3
Source dataset
uspto-grants-1994_05
Patent number
US05308820

Reaction notes

Loading…