Hydrazine hydrate (1:1) → (S)-2-Amino-5,5-dimethoxypentanoic acid, methyl ester

HRID 1292644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292644
C1(=O)[N:5]([C@@H:6]([CH2:11][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[C:7]([O:9][CH3:10])=[O:8])C(=O)C2=CC=CC=C12.O.NN>CO>[NH2:5][C@@H:6]([CH2:11][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[C:7]([O:9][CH3:10])=[O:8]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 10914214(S)-2-Phthalimido-5,5-dimethoxypentanoic acid, methyl ester

Produkt 1

HCID 642239(S)-2-Amino-5,5-dimethoxypentanoic acid, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(S)-2-Phthalimido-5,5-dimethoxypentanoic acid, methyl ester [prepared as described in Example 4 (f), 3.35 g., 10.43 mmol.) in methanol (70 ml.) was treated with hydrazine monohydrate (531 μl., 10.95 mmol., 1.05 eq.) and the solution was stirred at room temperature for 6 days. The mixture was filtered and the solid was washed with methanol. The filtrate was concentrated, triturated with methylene chloride, filtered again, concentrated, and dried in vacuo to yield 1.89 g. of title product as a cloudy oil. TLC (10% methanol in methylene chloride) Rf =0.39.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with methanol
  3. concentrationThe filtrate was concentrated
  4. customtriturated with methylene chloride
  5. filtrationfiltered again
  6. concentrationconcentrated
  7. customdried in vacuo
  8. customto yield 1.89 g

Quellen und Nachweise

ORD-Eintrag
ord-995df656a2c044c9a6d827499d186138
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756832

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