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1,2-Dichloroethane → (S)-tert-butyl 3-((R)-2-(pent-4-enoyloxy)-2-phenylethylcarbamoyl)hex-5-enoate

HRID 41071
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 41071
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].C(Cl)CCl.O[C@H:13]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:14][NH:15][C:16]([C@@H:18]([CH2:27][CH:28]=[CH2:29])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17].CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:1]([O:7][C@H:13]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:14][NH:15][C:16]([C@@H:18]([CH2:27][CH:28]=[CH2:29])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5]
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Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 611384-Pentenoic acidHCID 81531DiisopropylethylamineHCID 67312340(S)-tert-butyl 3-((R)-2-hydroxy-2-phenylethylcarbamoyl)hex-5-enoate

Produkt 1

HCID 67310751(S)-tert-butyl 3-((R)-2-(pent-4-enoyloxy)-2-phenylethylcarbamoyl)hex-5-enoateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-pentenoic acid (0.335 mL, 3.28 mmol) in DMF (31.6 mL) cooled in an ice/water bath was added EDC (630 mg, 3.28 mmol) and the resulting solution was stirred 30 min. (S)-tert-butyl 3-((R)-2-hydroxy-2-phenylethylcarbamoyl)hex-5-enoate (730 mg, 2.19 mmol), iPr2NEt (1.14 mL, 6.57 mmol) and DMAP (26.7 mg, 0.219 mmol) were subsequently added and the reaction mixture was slowly warmed to rt and stirred for 16 h at which point LC-MS analysis indicated complete consumption of starting material. The reaction mixture was diluted with saturated NH4Cl and EtOAc and the layers separated. The aqueous was extracted 2× with EtOAc and the combined organic extracts were washed with 1N HCl and brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified using silica gel chromatography (MeOH/CH2Cl2 gradient) to yield 670 mg of desired product as a colorless oil in 74% yield. LRMS (M+Na)+: 430.0.

Aufarbeitung

  1. additionwere subsequently added
  2. customconsumption of starting material
  3. additionThe reaction mixture was diluted with saturated NH4Cl and EtOAc
  4. customthe layers separated
  5. extractionThe aqueous was extracted 2× with EtOAc
  6. washthe combined organic extracts were washed with 1N HCl and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-4b3c48075aa44cf38924fdf68a33a632
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08530456B2

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