Sodium Hydroxide → N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine

HRID 259968Notes

Reaction equation

HRID 259968 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][N:5]([CH2:17][C@@H:18]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:19]([CH3:22])[CH2:20][CH3:21])[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]([NH:23][C@@H:18]([C@@H:19]([CH3:22])[CH2:20][CH3:21])[CH2:17][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])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10526565N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester

Product 1

HCID 22861722N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester (2.61 g, 6.10 mmol) was dissolved in MeOH (50 ml) and 1N NaOH (24.4 ml, 24.4 mmol) was added. The mixture was stirred at ambient temperature for 4 h and concentrated. The resulting residue was dissolved in water (25 ml) and neutralized with 1N HCl (24.4 ml). The aqueous layer was washed with EtOAc (3×50 ml). The organic layers were combined, dried with Na2SO4, filtered, and concentrated to give the product. 1H NMR (CD3OD) δ8.43 (1H, d, J=6Hz), 7.97 (2H, t, J=6 Hz) 7.75-7.48 (4H, m), 4.96 (1H, d, J=12Hz), 4.72 (1H, d, J=12 Hz), 3.80-3.58 (3H, m), 3.49-3.40 (1H, dd,, J=3 and 12 Hz), 3.03 (1H, dd, J=3 and 12 Hz), 1.42 (9H, s,), 1.37-1.28 (2H, m), 1.80-1.00 (1H, m), 0.94-0.78 (6H, m,) ppm.

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in water (25 ml)
  3. washThe aqueous layer was washed with EtOAc (3×50 ml)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the product

Sources & evidence

ORD record
ord-ac9d302ce0e740da9760a95a996c9e64
Source dataset
uspto-grants-1996_06
Patent number
US05523456

Reaction notes

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