1,2-Dichloroethane → Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamate

HRID 1908275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908275
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:10]([OH:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:22]1([NH2:25])[CH2:24][CH2:23]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>ClCCl>[CH:22]1([NH:25][C:11](=[O:13])[CH:10]([OH:14])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:24][CH2:23]1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 34203793-tert-Butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

Produkt 1

HCID 66645006Tert-butyl 4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamateAusbeute 114,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid (3 g, 10.16 mmol), cyclopropanamine (780 μL, 11.26 mmol) in dichloromethane (70 ml) at 5° C. EDC (2.4 g, 12.52 mmol), HOBt (1.9 g, 12.41 mmol) and Et3N (3 ml, 21.52 mmol) were added and the mixture stirred at room temperature for 48 h. After completion of reaction dichloromethane (100 ml) was added, the solution washed with water and brine, dried, filtered off with suction and concentrated to give 3.9 g of a brown oil which was purified further via chromatography on silica gel (eluent: CH2Cl2+5-30% (v/v) methanol). After evaporation of the combined product fractions 0.82 g of a pale oil were obtained; ESI-MS [M-Boc+H]±: 235.1.

Aufarbeitung

  1. customat 5° C
  2. additionwas added
  3. washthe solution washed with water and brine
  4. customdried
  5. filtrationfiltered off with suction
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-908b1fc04e6349fcbf64d8ff0c4dcf4c
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598211B2

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