Methanol → (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(pyridin-3-yl)propanoic acid

HRID 234657Notes

Reaction equation

HRID 234657 reaction equation
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:10]([O:12]C)=[O:11])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].CO>C(#N)C>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 131719806HCID 131719806, compound

Product 1

HCID 18392522(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(pyridin-3-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.5 g of Z-Pal-OMe (18.2 mMol) are dissolved in 100 ml of acetonitrile, mixed with 20 ml of 1N NaOH and stirred for 3 hours at ambient temperature. The mixture is neutralised by adding 20 ml of 1N NaOH, the solvent is largely removed on the rotary evaporator and the solid residue is mixed with ice cold water. After suction filtering the mixture is washed with a little water and the residue is dried in the desiccator whereby Z-Pal-OH is obtained in the form of white crystals. M.p.: 82° C.; [α]D20 (MeOH)=-9.4°.

Workup

  1. customthe solvent is largely removed on the rotary evaporator
  2. additionthe solid residue is mixed with ice cold water
  3. filtrationAfter suction filtering the mixture
  4. washis washed with a little water
  5. dry with materialthe residue is dried in the desiccator whereby Z-Pal-OH
  6. customis obtained in the form of white crystals

Sources & evidence

ORD record
ord-a6c21e51b83c4b5081ff7c22d7552590
Source dataset
uspto-grants-1997_01
Patent number
US05596000

Reaction notes

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