Propionitrile → tert-butyl ((2S)-1-((4-(benzyloxy)-5-nitropyrimidin-2-yl)oxy)propan-2-yl)carbamate

HRID 2277292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277292
[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(#N)CC>O>[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]=[C:11]([O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH3:22])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 7854PropionitrileHCID 62657Potassium Phosphate, TribasicHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 867313744-(Benzyloxy)-2-chloro-5-nitropyrimidine

Produkt 1

HCID 86731375tert-butyl ((2S)-1-((4-(benzyloxy)-5-nitropyrimidin-2-yl)oxy)propan-2-yl)carbamateAusbeute 16,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 4-(benzyloxy)-2-chloro-5-nitropyrimidine (670 mg), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (530 mg), potassium phosphate (642 mg) and propionitrile (10 mL) was stirred at 50° C. for 1 hr, and then at 100° C. for 5 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (170 mg).

Aufarbeitung

  1. waitat 100° C. for 5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4a56d5ca7e784656be327c9022d87d26
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133129B2

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