N-Methylbenzylamine → Z-Pal-N(Me)Bzl

HRID 1458203Notes

Reaction equation

HRID 1458203 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:35][NH:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:36]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH3:35])=[O:12])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 18392522(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(pyridin-3-yl)propanoic acid

Product 1

HCID 131719807Z-Pal-N(Me)Bzl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 g of Z-Pal-OH (8.7 mMol) are dissolved in 50 ml of THF, mixed with 1.55 g CDI (9.5 mMol), stirred for 45 minutes at ambient temperature, then mixed with 1.12 ml of N-methyl-benzylamine (8.7 mMol) and stirred for a further 64 hours at ambient temperature. The reaction mixture is concentrated on the rotary evaporator, the residue is taken up in ethyl acetate, extracted once with cold water and once with 10% NaCl solution. The organic phase is filtered, concentrated and chromatographed over a silica gel column by means of ether as eluant. Z-Pal-N(Me)Bzl is obtained as colourless oil from the eluant.

Workup

  1. stirringstirred for a further 64 hours at ambient temperature
  2. concentrationThe reaction mixture is concentrated on the rotary evaporator
  3. extractionextracted once with cold water and once with 10% NaCl solution
  4. filtrationThe organic phase is filtered
  5. concentrationconcentrated
  6. customchromatographed over a silica gel column by means of ether as eluant

Sources & evidence

ORD record
ord-e68d396924c34b08bee46509522ed6d4
Source dataset
uspto-grants-1998_12
Patent number
US05849918

Reaction notes

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