Triethylamine → HCID 67437196, Verbindung

HRID 1968882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968882
[F:1][C:2]1[N:7]=[C:6]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=O)[CH:5]=[CH:4][CH:3]=1.[C:14]([O:18][C:19](=[O:35])[NH:20][C@H:21]([CH2:26][NH:27][C:28]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=1)[C@@H:22]([CH3:25])[CH2:23][CH3:24])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[C:14]([O:18][C:19](=[O:35])[NH:20][C@H:21]([CH2:26][N:27]([C:28]1[CH:29]=[CH:30][C:31]([Br:34])=[CH:32][CH:33]=1)[C:11]([C@@H:9]1[CH2:10][C@H:8]1[C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=1)=[O:13])[C@@H:22]([CH3:25])[CH2:23][CH3:24])([CH3:16])([CH3:17])[CH3:15]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 67114406HCID 67114406, VerbindungHCID 67436431HCID 67436431, Verbindung

Produkt 1

HCID 67437196HCID 67437196, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A mixture of trans-2-(6-fluoro-pyridin-2-yl)-cyclopropanecarboxylic acid (120 mg, 0.55 mmol) in thionyl chloride (2 mL) was heated at reflux for over night. The mixture was concentrated and dried under high vacuum for 3 h. Then the residue was dissolved in DCM (3 mL) and added dropwise to a solution of {(1S,2S)1-[(4-Bromo-phenylamino)-methyl]-2-methyl-butyl}-carbamic acid tert-butyl ester (205 mg, 0.55 mmol) and triethyl amine (153 uL, 1.1 mmol) in DCM (3 mL). The resulting mixture was stirred at rt for overnight. The reaction mixture was concentrated and the residue was subjected to ISCO (12 g column, 0-40% EtOAc in hexane over 25 min.) to give the desired product (235 mg, 80%). MS (MH+ 534 and 536).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for over night
  3. concentrationThe mixture was concentrated
  4. customdried under high vacuum for 3 h
  5. dissolutionThen the residue was dissolved in DCM (3 mL)
  6. concentrationThe reaction mixture was concentrated
  7. customwas subjected to ISCO (12 g column, 0-40% EtOAc in hexane over 25 min.)

Quellen und Nachweise

ORD-Eintrag
ord-6b0204a809594c85ad2af734bdd7646e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426414B2

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