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

HRID 267077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 267077
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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester (7, 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) δ 8.43 (1H, d, J=6 Hz), 7.97 (2H, t, J=6 Hz) 7.75-7.48 (4H, m), 4.96 (1H, d, J=12 Hz), 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bf80c84c5a734b97b26d8612086739c5
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652257

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