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Bromotrichloromethane → (R)-methyl 2-(1-(tert-butoxycarbonylamino)ethyl)oxazole-4-carboxylate

HRID 245938
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 245938
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][O:8][C:7]([C@H:10]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:11])=[N:6]1)=[O:4].C1CCN2C(=NCCC2)CC1.BrC(Cl)(Cl)Cl>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C@H:10]([NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH3:11])[O:8][CH:9]=1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 712798212-((R)-1-tert-butoxycarbonylamino-ethyl)-4,5-dihydrooxazole-4-carboxylic acid methyl ester

Produkt 1

HCID 68671221(R)-methyl 2-(1-(tert-butoxycarbonylamino)ethyl)oxazole-4-carboxylateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

In a round-bottomed flask, 2-((R)-1-tert-butoxycarbonylamino-ethyl)-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (337 mg, 1.18 mmol) was dissolved in dichloromethane (11 ml). The solution was cooled to −16° C. (NaCl/ice bath) and DBU (0.35 ml, 2.32 mmol) was added. After 5 min, bromotrichloromethane (0.13 ml, 1.33 mmol) was added and the reaction mixture was allowed slowly to warm to room temperature and stirred for 4 days. The reaction was quenched with 0.1 M aqueous HCl and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to afford 152 mg (48%) of 2-((R)-1-tert-butoxycarbonylamino-ethyl)-oxazole-4-carboxylic acid methyl ester as an off-white solid.

Aufarbeitung

  1. additionwas added
  2. customThe reaction was quenched with 0.1 M aqueous HCl
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-d1203247537745eb862daa5a76e28614
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658646B2

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