Benzyl Alcohol → HCID 178525875, compound

HRID 1195129Notes

Reaction equation

HRID 1195129 reaction equation
[OH2:1].[N+]([C:5]1C=C([N+]([O-])=O)C=C[C:6]=1[NH:14][C@H:15]([C:22]([OH:24])=[O:23])[CH2:16][C:17]1[N:21]=[CH:20][NH:19][CH:18]=1)([O-])=O.C([OH:32])C1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[C:5]([CH2:6][NH:14][C@H:15]([C:22]([OH:24])=[O:23])[CH2:16][C:17]1[N:21]=[CH:20][NH:19][CH:18]=1)([OH:32])=[O:1]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 178526956HCID 178526956, compound

Product 1

HCID 178525875HCID 178525875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.2 g of Nα -t-butoxycarbonyl-Nim -2,4-dinitrophenyl-L-histidine monohydrate, 0.62 ml of benzyl alcohol, 1.03 g of N,N'-dicyclohexylcarbodiimide and 1.53 g of 1-hydroxybenzotriazole in 20 ml of methylene chloride was stirred overnight at ambient temperature. The mixture was then filtered and the solid rinsed with methylene chloride. The filtrates were combined and concentrated under vacuum. Chromatography of the residue over silica gel (gradient 1% to 2% methanol in methylene chloride) provided 1.76 g of the title compound.

Workup

  1. filtrationThe mixture was then filtered
  2. washthe solid rinsed with methylene chloride
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-36f73289c2b24db39b98edfc50344ed7
Source dataset
uspto-grants-1992_05
Patent number
US05110799

Reaction notes

Loading…