N,O-Dimethylhydroxylamine → 1,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

HRID 649728

Reaktionsgleichung

Reaktionsgleichung von HRID 649728
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][NH:21][O:22][CH3:23].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:23][O:22][N:21]([CH3:20])[C:10](=[O:12])[C@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[NH:1][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Komponenten

6

Edukt 4

HCID 14232N,O-DimethylhydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Produkt 1

HCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of Boc-Phe-OH 5.1 (2.0 g, 7.53 mmol) and N,O dimethylhydroxylamine (808 mg, 8.29 mmol) in DCM (38 ml) was added TEA (2.2 ml, 15.8 mmol) and HOBT (1.27 g, 8.29 mmol). After cooling to 0° C., EDCI (1.59 g, 8.29 mmol) was added in one portion, and the reaction was stirred overnight, warming to room temperature. The reaction was concentrated in vacuo, diluted with EthOAc (150 ml), and washed with H2O, 1 N KHSO4, 1 N NaHCO3 and brine. After drying over Na2SO4, filtering, and concentrating in vacuo, the residue was purified by flash chromatography to give the title compound as an oil in 88% yield. Rf=0.35 (50% EthOAc/hexane). 1H NMR (300 MHz, CDCl3) δ7.28 (d, 2H, J=7.4 Hz), 7.24 (t, 1H, J=6.8 Hz), 7.17 (d, 2H, 7.1 Hz), 5.18 (d, 1H, J=7.4 Hz), 4.9 (dd, 1H, J=7.0, 11.9 Hz), 3.66 (s, 3H), 3.16 (s, 3H), 3.05 (dd, 1H, J=6.0, 13.6 Hz), 2.87 (dd, 1H, J=7.0, 13.6 Hz), 1.39 (s, 9H).

Aufarbeitung

  1. temperaturewarming to room temperature
  2. concentrationThe reaction was concentrated in vacuo
  3. additiondiluted with EthOAc (150 ml)
  4. washwashed with H2O, 1 N KHSO4, 1 N NaHCO3 and brine
  5. dry with materialAfter drying over Na2SO4
  6. filtrationfiltering
  7. concentrationconcentrating in vacuo
  8. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bd070c42e5024da69a098affb66e5c43
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06270957B1

Verknüpfte Notizen

Wird geladen…