Sodium Hydroxide → HCID 67852548, compound

HRID 2226418Notes

Reaction equation

HRID 2226418 reaction equation
C([O:3][C:4]([CH:6]([NH:15][C@H:16]([C:18]([N:20]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[C:28]([OH:30])=[O:29])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([CH:6]([NH:15][C@H:16]([C:18]([N:20]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[C:28]([OH:30])=[O:29])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54481920HCID 54481920, compound

Product 1

HCID 67852548HCID 67852548, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[N-(1-ethoxycarbonyl-3-phenylpropyl) (S)-alanyl]azacyclooctane-2(S)-carboxylic acid (prepared as described in Example 41) in ethanol, add 0.25N sodium hydroxide. After three hours, concentrate the reaction mixture and absorb it on an XAD-2 resin column and elute with water and then with methanol. Concentrate the methanol eluant to give a residue and absorb this residue on a silica gel column and elute with chloroform:methanol: 14% ammonium hydroxide 1:1:1. Concentrate the desired eluant fractions to obtain the title compound.

Workup

  1. concentrationconcentrate the reaction mixture
  2. customabsorb it on an XAD-2 resin column
  3. washelute with water
  4. concentrationConcentrate the methanol eluant
  5. customto give a residue
  6. customabsorb this residue on a silica gel column
  7. washelute with chloroform
  8. concentrationConcentrate the desired eluant fractions

Sources & evidence

ORD record
ord-41b2c086620449348bdc8cb6783fe5e9
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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