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1-Hydroxybenzotriazole → [3-(2-Amino-3,6-dimethoxy-phenylcarbamoyl)-propyl]-methyl-carbamic acid benzyl ester

HRID 453711
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 453711
[CH2:1]([O:8][C:9]([N:11]([CH3:18])[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[C:42]([NH2:48])[C:41]=1[NH2:49]>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(Cl)CCl>[CH2:1]([O:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][CH2:14][C:15](=[O:17])[NH:48][C:42]1[C:43]([O:46][CH3:47])=[CH:44][CH:45]=[C:40]([O:39][CH3:38])[C:41]=1[NH2:49])[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 116296603,6-Dimethoxybenzene-1,2-diamineHCID 190283044-(((Benzyloxy)carbonyl)(methyl)amino)butanoic acid

Produkt 1

HCID 66899923[3-(2-Amino-3,6-dimethoxy-phenylcarbamoyl)-propyl]-methyl-carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 111,2-DichloroethaneLösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3.1 g of 4-(benzyloxycarbonyl-methyl-amino)-butyric acid in 80 mL DCM were added 6.5 mL of DIPEA, 1.8 g of HOBt, 2.6 g of EDC and 154 mg of DMAP. After stirring for 10 min, 2.1 g of 3,6-dimethoxy-benzene-1,2-diamine, dissolved in 20 mL DCM, were added and the mixture was stirred at rt overnight. The reaction was quenched with sat. aq. NaHCO3, the phases were separated and the organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to yield the crude title compound as black oil.

Aufarbeitung

  1. additionwere added
  2. stirringthe mixture was stirred at rt overnight
  3. customThe reaction was quenched with sat. aq. NaHCO3
  4. customthe phases were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-912d15ff2dd44d01bcd55d968668a820
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492555B2

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