Sodium Hydroxide → HCID 21307643, compound

HRID 363216Notes

Reaction equation

HRID 363216 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][N:5]([CH:17]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][NH:19]1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[C:27]([O:26][C:24]([CH:17]([C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][NH:19]1)[N:5]([CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:4][C:3]([OH:31])=[O:2])=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21307645HCID 21307645, compound

Product 1

HCID 21307643HCID 21307643, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(t-Butoxycarbonylpiperidin-2(S)-ylmethyl)-N-(1-naphthylmethyl)glycine methyl ester (3.71 g, 8.7 mmol) was dissolved in MeOH (130 ml) in an ice-H2O bath, and 1N NaOH (43.5 ml, 43.5 mmol) was added. The mixture was stirred at ambient temperature for 5 h and concentrated. The resulting residue was dissolved in H2O (50 ml) and neutralized with 1N HCl (43.5 ml). The aqueous layer was washed with EtOAc (3×75 ml). The organic layers were combined, dried (MgSO4), filtered, and concentrated to give the title compound as a white foam.

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in H2O (50 ml)
  3. washThe aqueous layer was washed with EtOAc (3×75 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-281322a5835442f29376c91042e41040
Source dataset
uspto-grants-1999_02
Patent number
US05872135

Reaction notes

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