N-Methylbenzylamine → Z-Pal-N(Me)Bzl

HRID 234658Notes

Reaction equation

HRID 234658 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. [α]D20 (MeOH )=-0.3°.

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-062cf6732320403593b9b40f0fe0df99
Source dataset
uspto-grants-1997_01
Patent number
US05596000

Reaction notes

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