Triethylamine → tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoate

HRID 25686

Reaktionsgleichung

Reaktionsgleichung von HRID 25686
[C:1]([O:5][C:6](=[O:14])[C@@H:7]([NH2:13])[C@@H:8]([OH:12])[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:22]([O:29][C:30](ON1C(=O)CCC1=O)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C:30]([NH:13][C@@H:7]([C@@H:8]([OH:12])[CH:9]([CH3:10])[CH3:11])[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:14])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 15408106(2S,3S)-2-amino-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

Produkt 1

HCID 59065895tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoateAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (2S,3S)-2-amino-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester (297 mg, 1.37 mmol) and triethylamine (139 mg, 1.37 mmol) in anhydrous methylene chloride (2 ml) was cooled to 0° C. under a nitrogen atmosphere. To this solution was added N-(benzyloxycarbonyloxy)-succinimide (343 mg, 1.37 mmol). The resulting mixture was warmed to room temperature and stirred for 15 hours. The reaction mixture was partitioned between ether and water. The organic layer was washed with cold 1N hydrochloric acid and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo, to provide tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]-amino}-3-hydroxy-4-methylpentanoate (445 mg, 96%) as a yellow oil.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ether and water
  2. washThe organic layer was washed with cold 1N hydrochloric acid and saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f8d8c4522a1b4656b2cd8f3b4927d4b2
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858591B2

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