1,2-Dichloroethane → HCID 69284015, Verbindung

HRID 84823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84823
[C:1]([NH:8][C@@H:9]([C:17]([OH:19])=O)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C2[N:26]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:26][C:17](=[O:19])[C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 2755927(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-cyclohexylpropanoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 69284015HCID 69284015, VerbindungAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-Boc-β-cyclohexyl-D-alanine (1.00 g, 3.69 mmol) and HOBt hydrate (0.678 g, 4.43 mmol) in DMF (10 mL), EDC (0.850 g, 4.43 mmol) was added. The mixture was stirred for 60 min. Then conc. NH4OH (1.00 mL, ˜14.0 mmol) was added. It was stirred for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-tert-butyl 1-amino-3-cyclohexyl-1-oxopropan-2-ylcarbamate as a white solid (0.917 g).

Aufarbeitung

  1. stirringIt was stirred for 18 h
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1b762bd07a644c27995447681244cbd4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846928B2

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