1,2-Dichloroethane → HCID 58813160, Verbindung

HRID 1391706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391706
CCN(C(C)C)C(C)C.[CH2:10]([C@H:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([OH:16])=O)[CH:11]=[CH2:12].Cl.[NH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl>CN(C=O)C>[CH2:10]([C@H:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([NH:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:16])[CH:11]=[CH2:12]

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 58813156HCID 58813156, Verbindung

Produkt 1

HCID 58813160HCID 58813160, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Step B (1): DIEA (1.35 mL, 9.9 mmol) was added to a mixture of (S)-2-allylhexanoic acid (300 mg, 1.92 mmol), methyl 2-aminoacetate hydrochloride (254 mg, 2.02 mmol), EDC (387 mg, 2.02 mmol), HOBt (273 mg, 2.02 mmol) in DMF (15 mL) at room temperature. The mixture was stirred for 18 h. Poured the reaction mixture into 200 mL 1 M HCl. Extracted with EtOAc/Hex (95:5) (2×200 mL). Washed combined organic extracts with brine, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (5-50% EtOAc/hexanes linear gradient) to give (S)-methyl 2-(2-allylhexanamido)acetate 360 mg (83% yield) as white solid: ESI (M+H)+=228.2; 1H NMR (500 MHz, CDCl3) δ 5.90 (s, 1H), 5.64-5.85 (m, 1H), 4.95-5.14 (m, 2H), 4.04 (dd, J=5.04, 2.29 Hz, 2H), 3.75 (s, 3H), 2.28-2.46 (m, 1H), 2.07-2.29 (m, 2H), 1.62-1.64 (m, 1H), 1.46-1.47 (m, 1H), 1.18-1.36 (m, 4H), 0.87 (t, J=6.87 Hz, 3H).

Aufarbeitung

  1. extractionExtracted with EtOAc/Hex (95:5) (2×200 mL)
  2. washWashed
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (5-50% EtOAc/hexanes linear gradient)

Quellen und Nachweise

ORD-Eintrag
ord-9e89ec9dd99a4d778aac577667933761
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338974B2

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