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

HRID 41070

Reaktionsgleichung

Reaktionsgleichung von HRID 41070
[C:1]([O:5][C:6](=[O:15])[CH2:7][C@H:8]([CH2:12][CH:13]=[CH2:14])[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:26]C=2C=1.N[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C@H:37]([OH:39])[CH3:38].CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[OH:39][C@H:37]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:31]=1)[CH2:38][NH:26][C:9]([C@@H:8]([CH2:12][CH:13]=[CH2:14])[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:15])=[O:11]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10920569(R)-2-amino-phenylethanolHCID 16053367(S)-2-[2-(tert-Butoxy)-2-oxoethyl]pent-4-enoic Acid

Produkt 1

HCID 67312340(S)-tert-butyl 3-((R)-2-hydroxy-2-phenylethylcarbamoyl)hex-5-enoateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(2-tert-butoxy-2-oxoethyl)pent-4-enoic acid (0.947 g, 4.42 mmol) (described by Stanton, B. Z. et al. Nat. Chem. Biol. 2009, 5, 154-156) in DMF (31.6 mL) cooled in an ice/water bath was added EDC (1.27 g, 6.63 mmol) and HOBt (0.896 g, 6.63 mmol) and the resulting solution was stirred 30 min. (R)-2-amino-phenylethanol (0.667 g, 4.86 mmol), iPr2NEt (2.31 mL, 13.3 mmol) and DMAP (0.108 g, 0.884 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 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 1.25 g of desired product as a light yellow oil in 85% yield. LRMS (M+Na)+: 356.2.

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 1 N 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-fba568ae791d4759969f39512fca942b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530456B2

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