4-Methylmorpholine → HCID 67004356, Verbindung

HRID 1919176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919176
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)=[O:5].[C:13]([C:16]([CH2:23][Br:24])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])(O)=[O:14].CN1CCOCC1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C1COCC1>[Br:24][CH2:23][C:16]([O:17][CH2:18][CH3:19])([O:20][CH2:21][CH3:22])[C:13]([NH:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)=[O:5])=[O:14]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 30262702-amino-1-(3-bromophenyl)ethanone hydrochlorideHCID 130997963-Bromo-2,2-diethoxypropanoic acid

Produkt 1

HCID 67004356HCID 67004356, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The 2-amino-1-(3-bromophenyl)ethanone hydrochloride (4.6 g, 19 mmol), HO2CC(OEt)2CH2Br (5.0 g, 21 mmol), and NMM (12.5 mL, 113 mmol) were suspended in anhyd THF (270 mL) under N2 and PyBOP (10.8 g, 21 mmol) was added in one portion. The reaction mixture was stirred for 18 h and concentrated to ¼ vol and the precipitates were removed by filtration (HCl salt of NMM). The mother liquor was taken up in dichloromethane and washed with water. After concentration, the crude residue was subjected to flash chromatography (silica gel) eluting with 60% EtOAc/hexanes to give Intermediate J.1, 5.3 g (65%). 1H NMR (500 MHz, DMSO-d6): δ 8.27 (t, J=5.5 Hz, 1H), 8.14 (t, J=1.5 Hz, 1H), 8.00 (dt, J=7.9, 1.2 Hz, 1H), 7.87 (dd, J=8.8, 1.8 Hz, 1H), 7.51 (t, J=7.9 Hz, 1H), 4.65 (d, J=5.8 Hz, 2H), 3.67 (s, 2H) 3.58-3.46 (m, 4H), 1.18 (t, J=7.0 Hz, 6H). LCMS: 2.2 min; LRMS: Calcd. for C15H19Br2NO4: 435.98. Found: 435.98 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated
  2. customthe precipitates were removed by filtration (HCl salt of NMM)
  3. washwashed with water
  4. concentrationAfter concentration
  5. washeluting with 60% EtOAc/hexanes
  6. customto give Intermediate J.1, 5.3 g (65%)
  7. custom2.2 min

Quellen und Nachweise

ORD-Eintrag
ord-331ce07056b0446ba4719a54067e61c9
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618153B2

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