Acetic Acid → HCID 86753683, compound

HRID 361774Notes

Reaction equation

HRID 361774 reaction equation
[N:1]1([C:7]([C:9]2[CH:39]=[CH:38][C:12]([C:13]([NH:15][CH:16]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:17]([CH3:31])([CH3:30])[C:18]([N:20]3[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([O-:29])=[O:28])[CH2:22][CH2:21]3)=[O:19])=[O:14])=[CH:11][CH:10]=2)=[NH:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(=O)C>CO.[C].[Pd]>[N:1]1([C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:15][CH:16]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:17]([CH3:31])([CH3:30])[C:18]([N:20]3[CH2:21][CH2:22][CH:23]([CH2:26][C:27]([OH:29])=[O:28])[CH2:24][CH2:25]3)=[O:19])=[O:14])=[CH:38][CH:39]=2)=[NH:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86753684HCID 86753684, compound

Product 1

HCID 86753683HCID 86753683, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

The compound of Example 69, i.e. benzyl-N-(N-(4-(4-morpholinoimidoyl)benzoyl-β-phenyl-α,α-dimethyl-β-alanyl)-4-piperidineacetate (54 mg, 0.086 mmol) was dissolved in a 80% aqueous methanol solution (10 ml) containing 2% acetic acid. To the resulting solution was added 5% palladium carbon (10 mg) and the mixture was stirred overnight under a hydrogen atmosphere. After the solvent was distilled off, the residue was dissolved in a 1N aqueous solution of acetic acid and purified by HPLC in the same manner as in Example 44 to yield the titled compound (32 mg, 69%).

Workup

  1. distillationAfter the solvent was distilled off
  2. dissolutionthe residue was dissolved in a 1N aqueous solution of acetic acid
  3. custompurified by HPLC in the same manner as in Example 44

Sources & evidence

ORD record
ord-9d606714359d464d88a69eea6cc700ad
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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