1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → ((S)-1-[2-(6-bromopyridin-2-yl)-2-oxoethylcarbamoyl]ethyl}carbamic acid tert-butyl ester

HRID 1716509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716509
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=1)=[O:5].C([C:17]([NH:19][C@H:20]([C:22](O)=[O:23])[CH3:21])=[O:18])(C)(C)C.Cl.CN(C)[CH2:28][CH2:29][CH2:30]N=C=NCC.[OH2:37].ON1C2C=CC=C[C:42]=2N=N1>C(#N)C.O.C(N(CC)CC)C>[C:29]([O:37][C:17](=[O:18])[NH:19][C@H:20]([C:22](=[O:23])[NH:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=1)=[O:5])[CH3:21])([CH3:30])([CH3:42])[CH3:28]

Komponenten

8

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 42254381(S)-N-tert-butylcarbonylalanineHCID 534164172-Amino-1-(6-bromopyridin-2-YL)ethanone hydrochloride

Produkt 1

HCID 86607641((S)-1-[2-(6-bromopyridin-2-yl)-2-oxoethylcarbamoyl]ethyl}carbamic acid tert-butyl esterAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a suspension of 2-amino-1-(6-bromopyridin-2-yl)ethanone hydrochloride (500 mg, 1.99 mmol) obtained in Step 1 of example 6, (S)-N-tert-butylcarbonylalanine (376 mg, 1.99 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (379 mg, 1.99 mmol), 1-hydroxybenzotriazole monohydrate (305 mg, 1.99 mmol) in acetonitrile (11 ml), a solution of triethylamine (0.7 ml) in acetonitrile (4 ml) was added dropwise while ice-cooled for 15 minutes. After the mixture was stirred at the same temperature for 1 hour, water was added and extracted with ethyl acetate. After the organic layer was washed with water, a saturated brine, dried over magnesium sulfate, the residue obtained by vacuum concentration was purified by flash chromatography on silica gel (n-hexane:ethyl acetate=2:1) and the title compound (456 mg, 59%) was obtained.

Aufarbeitung

  1. temperaturecooled for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water
  4. dry with materiala saturated brine, dried over magnesium sulfate
  5. customthe residue obtained by vacuum concentration
  6. customwas purified by flash chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-adfa8a424aa74cfcb88b1c6175196bcb
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803801B2

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