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1,1'-Carbonyldiimidazole → (R)-ethyl 2-(3-(1-hydroxy-3-phenylpropan-2-yl)ureido)-4-methylthiazole-5-carboxylate

HRID 560541
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 560541
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[NH2:25][C@H:26]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:27][OH:28]>O1CCCC1>[OH:28][CH2:27][C@H:26]([NH:25][C:13](=[O:14])[NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
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Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 853475phenylalaninol, (R)-

Produkt 1

HCID 73213189(R)-ethyl 2-(3-(1-hydroxy-3-phenylpropan-2-yl)ureido)-4-methylthiazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (1.86 g, 10.0 mmol) in tetrahydrofuran (50 mL) was added 1,1′-carbonyldiimidazole (1.95 g, 12.0 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 17 hours, followed by the addition of (R)-(+)-2-amino-3-phenyl-1-propanol (2.00 g, 13.2 mmol). The reaction mixture was kept stirring at ambient temperature for 50 hours. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (200 mL) and washed with water and brine. The organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford the title compound in 88% (3.20 g): MS (ES+) m/z 364.4 (M+1).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was kept stirring at ambient temperature for 50 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  5. washwashed with water and brine
  6. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0b04c58388994db6a504952ada57d2cb
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063084B2

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