Benzyl Chloride → Poly(1-benzylhistidine)

HRID 1493877Notes

Reaction equation

HRID 1493877 reaction equation
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[Na].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N>[CH2:13]([N:6]1[CH:7]=[N:8][C:4]([CH2:3][C@@H:2]([C:9]([OH:11])=[O:10])[NH2:1])=[CH:5]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 5360545SodiumHCID 178419078HCID 178419078, compound

Product 1

HCID 193138Poly(1-benzylhistidine)

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

The product 1 was synthesized by treating a solution of L-histidine (80 g, 138 mmol) in liquid ammonia (600 mL) at -70° C. with sodium (36 g) and benzylchloride (48 mL, 416 mmol). The desired product crystallized from a water solution at pH 8 and, after recrystallization from ethanol/water, 7/3, was obtained in a 56% (52.2 g) yield: mp 234-238° C. (lit. mp 248-249° C. corr).

Workup

  1. customThe desired product crystallized from a water solution at pH 8
  2. customafter recrystallization from ethanol/water, 7/3
  3. customwas obtained in a 56% (52.2 g) yield

Sources & evidence

ORD record
ord-7582290ad16f46b0b28f93fd1989f755
Source dataset
uspto-grants-1991_06
Patent number
US05025027

Reaction notes

Loading…