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1,2-Dichloroethane → (S)-4-tert-butyl 1-((R)-2-pent-4-enamido-2-phenylethyl) 2-allylsuccinate

HRID 41075
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 41075
[C:1]([O:5][C:6](=[O:15])[CH2:7][C@H:8]([CH2:12][CH:13]=[CH2:14])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.O[CH2:21][C@H:22]([NH:29][C:30](=[O:35])[CH2:31][CH2:32][CH:33]=[CH2:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:12]([C@@H:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])[C:9]([O:11][CH2:21][C@H:22]([NH:29][C:30](=[O:35])[CH2:31][CH2:32][CH:33]=[CH2:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:10])[CH:13]=[CH2:14]
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Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 16053367(S)-2-[2-(tert-Butoxy)-2-oxoethyl]pent-4-enoic AcidHCID 67310926(R)-N-(2-hydroxy-1-phenylethyl)pent-4-enamide

Produkt 1

HCID 67310391(S)-4-tert-butyl 1-((R)-2-pent-4-enamido-2-phenylethyl) 2-allylsuccinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(2-tert-butoxy-2-oxoethyl)pent-4-enoic acid (684 mg, 3.19 mmol) in DMF (25 mL) cooled in an ice/water bath was added EDC (612 mg, 3.19 mmol) and the resulting solution was stirred for 30 min. (R)-N-(2-hydroxy-1-phenylethyl)pent-4-enamide (700 mg, 3.19 mmol), iPr2NEt (1.77 mL, 9.58 mmol), and DMAP (39.0 mg, 0.319 mmol) were subsequently added and the reaction mixture was stirred 16 h at which point LC-MS analysis indicated the presence of both starting material and desired product. The reaction mixture was diluted with saturated NH4Cl and EtOAc and the layers separated. The aqueous layer was extracted 2× with EtOAc and the combined organic extracts were washed with 1 N HCl and brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified using silica gel chromatography (MeOH/CH2Cl2 gradient) to yield 340 mg of product as a colorless oil in 26% yield. LRMS (M+Na)+: 438.4.

Aufarbeitung

  1. additionwere subsequently added

Quellen und Nachweise

ORD-Eintrag
ord-d71ae031ebc240d5ad4a4f7bf7f8a38e
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08530456B2

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