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Water → tert-butyl N-[isopropyl(2,2,2-trifluoroethylcarbamoyl)amino]carbamate

HRID 1502785
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1502785
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].Cl[C:8](Cl)([O:10]C(=O)OC(Cl)(Cl)Cl)Cl.[CH:19]([NH:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:21])[CH3:20].O>C(Cl)Cl>[CH:19]([N:22]([C:8](=[O:10])[NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])[NH:23][C:24]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:30])([CH3:21])[CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 94429TriphosgeneHCID 11217534N'-(propan-2-yl)(tert-butoxy)carbohydrazide

Produkt 1

HCID 86722583tert-butyl N-[isopropyl(2,2,2-trifluoroethylcarbamoyl)amino]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
3×

Versuchsvorschrift

2,2,2-Trifluoroethanamine (284 mg, 2.87 mmol), TEA (0.8 ml, 5.74 mmol)) in CH2Cl2 (6 mL) were added to the solution of triphosgene (298 mg, 1 mmol) in CH2Cl2 (8 mL) at −40° C. and the reaction mixture was stirred for 30 min tert-Butyl N-(isopropylamino)carbamate (JOC, 2013, 78, 3541-3552.) (500 mg, 2.87 mmol) in CH2Cl2 (4 mL) was then added to the reaction mixture at −40° C. and stirred at ambient temperature—overnight. Water was added to the reaction mixture and it was extracted with CH2Cl2. The organic layer wad washed with brine, dried (Na2SO4), filtered and concentrated to afford the title compound as an off white solid (580 mg, crude): mp 90-94° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.70 (bs, 1H), 6.81 (t, J=6.3, 1H), 3.89-3.80 (m, 2H), 3.11-3.08 (m, 1H), 1.40 (s, 9H), 0.97 (d, J=6.0 Hz, 6H); ESIMS m/z 241.9 ([M-tert-Butyl]+).

Aufarbeitung

  1. additionwas then added to the reaction mixture at −40° C.
  2. extractionwas extracted with CH2Cl2
  3. washThe organic layer wad washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1888b7f5d7e94e25a731db1e96337582
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09210927B2

Notizen zur Reaktion

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