4-Methylmorpholine → Tert-butyl hex-5-enoate

HRID 965165

Reaktionsgleichung

Reaktionsgleichung von HRID 965165
[C:1]([O:5][C:6](=[O:15])[CH2:7][C@@H:8]([CH2:12][CH:13]=[CH2:14])C(O)=O)([CH3:4])([CH3:3])[CH3:2].N[C@H]1CC2=CN(C3C2=CC=CC=3)CCOCCNC1=O.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:15])[CH2:7][CH2:8][CH2:12][CH:13]=[CH2:14])([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10560578HCID 10560578, VerbindungHCID 67694341HCID 67694341, Verbindung

Produkt 1

HCID 15047738Tert-butyl hex-5-enoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-(R)-allyl-succinic acid 4-t-butyl ester (5 g, 0.00234 mol), 9-(S)-amino-4-oxa-1,7-diaza-tricyclo[9.6.1.012,17 ]octadeca-11(18),12,14,16-tetraen-8-one (6,38 g, 0.00234mol) in 50 mL DMF added HOBT (3.47 g, 0.026 mol), DMAP (80 mg), N-methylmorpholine (2.84 g, 0.028 mol), and EDCI (6.69 g, 0.035 mol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (300 mL) and washed with brine (2×100 mL), saturated NaHCO3 (2×100 mL) and brine (1×100 mL), and dried (MgSO4). Removal of the solvents gave 9 g of crude product. Column chromatographic purification (50% EtOAc/CH2Cl2) gave 7.5 g of pure (3R,9S)-3-(8-oxo-4-oxa-1,7-diaza-tricyclo[9.6.1.012,17 ]octadeca-11(18)12,14,16-tetraen-9-yl carbamoyl)-hex-5-enoic acid t-butyl ester, MS: 469(M+).

Aufarbeitung

  1. washwashed with brine (2×100 mL), saturated NaHCO3 (2×100 mL) and brine (1×100 mL)
  2. dry with materialdried (MgSO4)
  3. customRemoval of the solvents
  4. customgave 9 g of crude product
  5. customColumn chromatographic purification (50% EtOAc/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-08f2c05b10264987a882e8a0deec87c6
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773428

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