1,2-Dichloroethane → (R)-tert-butyl 1-amino-3-(benzyloxy)-1-oxopropan-2-ylcarbamate

HRID 2201049

Reaktionsgleichung

Reaktionsgleichung von HRID 2201049
[C:1]([NH:8][C@@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=C2[N:28]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:28][C:19](=[O:21])[C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 7216902(R)-tert-butyl 1-amino-3-(benzyloxy)-1-oxopropan-2-ylcarbamateAusbeute 87,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-Boc-O-benzyl-D-serine (510 mg, 1.72 mmol) and HOBt hydrate (317 mg, 2.07 mmol) in DMF (9 mL), EDC (432 mg, 2.25 mmol) was added. The mixture was stirred for 60 min. Then conc. NH4OH (0.600 mL, ˜8.40 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-(benzyloxy)-1-oxopropan-2-ylcarbamate (444 mg).

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-1003d443af964ada8ae07771af917bb3
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359375B2

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