Triacetoxyperiodinane → 3(S)-(tert-butoxyformamido)-2-oxo-N-(1(S)-phenylpropyl)heptanamide

HRID 635639

Reaktionsgleichung

Reaktionsgleichung von HRID 635639
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:46][CH2:47][CH2:48][CH3:49])[C@H:32]([OH:45])[C:33]([NH:35][C@H:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:37][CH3:38])=[O:34])=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl.C(OCC)(=O)C>[C:23]([O:27][C:28]([NH:30][C@@H:31]([CH2:46][CH2:47][CH2:48][CH3:49])[C:32](=[O:45])[C:33]([NH:35][C@H:36]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:37][CH3:38])=[O:34])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Komponenten

5

Edukt 2

HCID 159087Triacetoxyperiodinane2×HCID 206399793(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide

Produkt 1

HCID 206399773(S)-(tert-butoxyformamido)-2-oxo-N-(1(S)-phenylpropyl)heptanamideAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.383 g of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one was added to a solution of 0.285 g of 3(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide in 20 ml of dichloromethane. The mixture was stirred at room temperature for 30 minutes and then a further 30 mg of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one were added. The mixture was stirred at room temperature for 30 minutes and then diluted with ethyl acetate. The solution was extracted with a solution of 10 g of sodium thiosulphate in 40 ml of saturated sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica gel using 20% ethyl acetate in hexane for the elution to give 200 mg of 3(S)-(tert-butoxyformamido)-2-oxo-N-(1(S)-phenylpropyl)heptanamide, MS: m/e 377.1 [M+H]+.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. extractionThe solution was extracted with a solution of 10 g of sodium thiosulphate in 40 ml of saturated sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel using 20% ethyl acetate in hexane for the elution

Quellen und Nachweise

ORD-Eintrag
ord-1f96bf04c2014bce81f9c620da14c3a0
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187905B1

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