Water → tert-butyl N-((1S)-1-cyanoethyl)carbamate

HRID 1508278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508278
[NH2:1][C:2](=O)[C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C)C=O>[C:2]([C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4])#[N:1]

Komponenten

5

Edukt 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 7015295Boc-Ala-NH2

Produkt 1

HCID 638383tert-butyl N-((1S)-1-cyanoethyl)carbamateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl [(1S)-2-amino-1-methyl-2-oxoethyl]carbamate (Step 1, 0.7 g, 0.004 mol) in N,N-dimethylformamide (5 mL) was added 343 mg of cyanuric chloride (0.00186 mol) at once. The reaction mixture was stirred for 4 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with EtOAc in hexane (30-50%) to yield the desired product (400 mg, 63%). 1H-NMR (300 MHz, DMSO-d6): 7.74 (d, J=7.0 Hz, 1H), 4.48 (m, 1H), 1.40 (s, 9H), 1.35 (d, J=7.0 Hz, 3H).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on a silica gel column with EtOAc in hexane (30-50%)

Quellen und Nachweise

ORD-Eintrag
ord-dd77eb606b1140678a9674ffd9f7b3b1
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221824B2

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