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Potassium Carbonate → 3-Benzyloxycarbonylamino 6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 567799
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 567799
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CC(=O)CC>[CH2:12]([O:11][C:10]([NH:9][C:5]1[C:6](=[O:8])[N:7]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 100838403-Benzyloxycarbonylamino-6-methyl-2-pyridone

Produkt 1

HCID 102486933-Benzyloxycarbonylamino 6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinoneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl Ketone
Lösungsmittel
2×

Versuchsvorschrift

A slurry of benzyl N-(6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)carbamate (preparation 3) (20 g, 78 mmol) in 2-butanone (500 ml) was treated with K2CO3 (53.9 g, 94 mmol) and further 2-butanone (100 ml). The resultant mixture was treated cautiously with tert-butyl 2-bromoacetate (15.2 ml, 94 mmol) and stirred at room temperature for 18 hr. The solvent was evaporated and the crude material was partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate, the combined organic layers washed with sat aq brine and dried over Na2SO4. Removal of the drying agent by filtration followed by evaporation of the solvent gave the crude product which was purified by recrystallisation from ethyl acetate:hexane to give the desired product (white solid, 15.1 g, 52%). 1H NMR (CDCl3) δ: 1.40 (s, 9H), 2.20 (s, 3H), 4.70 (s, 2H), 5.20 (s, 2H), 6.05 (d, 1H), 7.40 (m, 5H), 7.70 (s, br, 1H), 7.90 (d, 1H). LRMS m/z=373.6 (M+1)+.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe crude material was partitioned between ethyl acetate and water
  3. washThe aqueous layer was washed with ethyl acetate
  4. washthe combined organic layers washed with sat aq brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the drying agent
  7. filtrationby filtration
  8. customfollowed by evaporation of the solvent
  9. customgave the crude product which
  10. customwas purified by recrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-489d1be9a87b48c487ee01d5fd602fa0
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06180627B2

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