4-tert-Butylbenzoyl chloride → HCID 73939388, Verbindung

HRID 1622985

Reaktionsgleichung

Reaktionsgleichung von HRID 1622985
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].CCN(C(C)C)C(C)C.[C:25]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([C:29]1[CH:30]=[CH:31][C:32]([C:33]([NH:1][C@@H:2]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[CH:12][CH:13]=2)[C:3]([O:5][CH3:6])=[O:4])=[O:34])=[CH:36][CH:37]=1)([CH3:28])([CH3:26])[CH3:27]

Komponenten

5

Edukt 3

HCID 743724-tert-Butylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 54521608(S)-methyl 2-amino-3-(4-cyanophenyl)propanoate

Produkt 1

HCID 73939388HCID 73939388, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Prepared using General Procedure 3: To the solution of (S)-methyl 2-amino-3-(4-cyanophenyl)propanoate (789.2 mg, 3.32 mmol) in DCM (15 mL) and DIEA (1.29 g, 9.96 mmol) was added 4-(tert-butyl)benzoyl chloride (981.3 mg, 4.99 mmol) at RT. The reaction was stirred for 2 h and the reaction was partitioned between DCM and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by chromatography (EA/hexanes) to afford 1.06 g (88%) of (S)-methyl 2-(4-(tert-butyl)benzamido)-3-(4-cyanophenyl)propanoate. LCMS-ESI (m/z) calculated for C22H24N2O3: 364.2; found 365.3 [M+H]+, tR=3.55 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 8.81 (d, J=8.0 Hz, 1H), 7.85-7.60 (m, 4H), 7.49 (dd, J=15.1, 8.4 Hz, 4H), 4.85-4.60 (m, 1H), 3.65 (s, 3H), 3.30-3.23 (m, 1H), 3.18 (dd, J=13.7, 10.6 Hz, 1H), 1.29 (s, 9H).

Aufarbeitung

  1. customPrepared
  2. customthe reaction was partitioned between DCM and saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography (EA/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-81aabca718ec42d889984d77301fbf24
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778923B2

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