Diisopropylethylamine → HCID 11674493, Verbindung

HRID 1866117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866117
[C:1]1([C@H:7]([CH2:11][CH3:12])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[F:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][C:57]=1[CH2:66][NH2:67]>CN(C)C=O>[F:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]([F:63])([F:64])[F:65])=[CH:58][C:57]=1[CH2:66][NH:67][C:8](=[O:10])[C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:11][CH3:12]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 5338392-Fluoro-5-(trifluoromethyl)benzylamineHCID 785329(S)-2-Phenylbutyric acidHCID 2724699PyBOP

Produkt 1

HCID 11674493HCID 11674493, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (S)-2-phenylbutanoic acid (1-d, 50 mg, 0.30 mmol, Sigma-Aldrich, Milwaukee, Wis.) and diisopropylethylamine (98 uL, 0.60 mmol) in N,N-dimethylformamide (1 mL) was treated at room temperature with benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBop, 158 mg, 0.30 mmol). After 15 min, (2-fluoro-5-(trifluoromethyl)phenyl)methanamine (1-g, 60 mg, 0.30 mmol, Synthesis, Inc., Wyndham, N.H.) was added. The reaction mixture was stirred for 3 h, partitioned between dichioromethane and 0.5N—NaOH. The aqueous layer was removed and the organic layer was washed with 0.5N—HCl. The aqueous layer was removed by filtering through a plastic frit. The organic layer was concentrated in vacuo to give the desired product (1-1); HRMS (M+1)=340.129; 1H NMR (500 MHz, CDCl3) δ7.49 (bs, 1H), 7.41 (d, 1H, J=6.5 Hz), 7.34-7.26 (m, 5H), 7.10 (t, 1H, J=9.0 Hz), 5.77 (bs, 1H), 4.47 (d, 1H, J=3.0 Hz), 3.30 (t, 2H, J=7.5 Hz), 2.22 (m, 1H), 1.82 (m, 1H), 0.89 (t, 3H, J=7.5 Hz).

Aufarbeitung

  1. custompartitioned between dichioromethane and 0.5N—NaOH
  2. customThe aqueous layer was removed
  3. washthe organic layer was washed with 0.5N—HCl
  4. customThe aqueous layer was removed
  5. filtrationby filtering through a plastic frit
  6. concentrationThe organic layer was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2f9658b55f0e4702ba1aac3a0b46e453
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629367B2

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