Sodium Hydroxide → Ammonium Hydroxide

HRID 2226415Notes

Reaction equation

HRID 2226415 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[C:24]([O:26]CC)=[O:25])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[NH4+:11].[OH-:8].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]1[C:24]([OH:26])=[O:25])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[C:24]([OH:26])=[O:25])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 131718676HCID 131718676, compound

Product 3

HCID 14923Ammonium HydroxideYield 7%HCID 18654881HCID 18654881, compoundHCID 18654882HCID 18654882, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.09 g of 1-[N-benzyloxycarbonyl-(S)-alanyl]azacyclooctane-2(R,S)-carboxylic acid, ethyl ester in 150 ml methanol, add 20 ml of 2.5 N sodium hydroxide and stir the mixture at room temperature for 18 hours. Concentrate the mixture under nitrogen, dilute the residue with ice-water and then make the mixture acidic with concentrated hydrochloric acid. Extract the aqueous solution with ethyl acetate and dry the organic phase over magnesium sulfate. Concentrate the organic phase to give a white residue. Place the residue on a column of silica gel (1000 ml, 60-200 mesh) and elute with chloroform:isopropanol:7% NH4OH (organic phase) to give 1-[N-benzyloxycarbonyl-(S)-alanyl]azacyclooctane-2(R)-carboxylic acid and 1-[N-benzyloxycarbonyl-(S)-alanyl]azacyclooctane-2(S)-carboxylic acid, as colorless oils.

Workup

  1. concentrationConcentrate the mixture under nitrogen
  2. additiondilute the residue with ice-water
  3. extractionExtract the aqueous solution with ethyl acetate
  4. dry with materialdry the organic phase over magnesium sulfate
  5. concentrationConcentrate the organic phase
  6. customto give a white residue
  7. washelute with chloroform

Sources & evidence

ORD record
ord-b7412231e2634964ac423f639d1f1ae6
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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