1,2-Dichloroethane → (1-Carbamoyl-2-isobutyl-cyclopropylmethyl)-carbamic acid tert-butyl ester

HRID 1297242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297242
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([C:17]([OH:19])=O)[CH2:12][CH:11]1[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:26]C=2C=1.CN1CCOCC1.C(Cl)CCl>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1([C:17](=[O:19])[NH2:26])[CH2:12][CH:11]1[CH2:13][CH:14]([CH3:16])[CH3:15])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 221827451-(Tert-butoxycarbonylamino-methyl)-2-isobutyl-cyclopropanecarboxylic acid

Produkt 1

HCID 69516040(1-Carbamoyl-2-isobutyl-cyclopropylmethyl)-carbamic acid tert-butyl esterAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1-(tert-butoxycarbonylamino-methyl)-2-isobutyl-cyclopropanecarboxylic acid (5.2 g, 19.2 mmol) in dry THF (190 mL) was added HOBt (2.85 g, 21.1 mmol), NMM (2.32 mL, 21.1 mmol) and EDC (4.0 g, 21.1 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 3 hours and quenched with concentrated ammonium hydroxide (16 mL). The reaction mixture was stirred at room temperature overnight. Excess of solvent was removed in vacuo and the residue was dissolved in EtOAc (200 mL). The organic layer was washed with 1N HCl, aqueous NaHCO3, brine and dried over Na2SO4. Evaporation of excess of solvent gave 3.5 g (69%) of (1-carbamoyl-2-isobutyl-cyclopropylmethyl)-carbamic acid tert-butyl ester as a colorless oil: 1H NMR (300 MHz, CD3OD) & 0.61 (dd, J=4.2, 6.5 Hz, 1H), 0.94 (d, J=5.0 Hz, 3H), 0.96 (d, J=5.0 Hz, 3H), 1.20 (m, 1H), 1.29 (dd, J=3.9, 8.7 Hz, 1H), 1.44 (s, 9H), 1.51 (m, 2H), 1.65 (m, 1H), 3.20 (d, J=15.2 Hz, 1H), 3.54 (d, J=15.2 Hz, 1H); 13C (75 MHz, CD3OD) δ 21.5, 23.2, 23.6, 27.4, 29.3, 30.3, 30.4, 39.3, 41.8, 80.9, 159.3, 179.9; MS (APCI) m/z271 [M+H]+.

Aufarbeitung

  1. customquenched with concentrated ammonium hydroxide (16 mL)
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. customExcess of solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in EtOAc (200 mL)
  5. washThe organic layer was washed with 1N HCl, aqueous NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation of excess of solvent

Quellen und Nachweise

ORD-Eintrag
ord-2725c8ccce71477eacc6fcb0bbbac680
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250433B2

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