Trifluoroacetic acid → 4-{3-methoxy-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoic Acid

HRID 1860679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860679
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([O:25]CC)=[O:24])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.FC(F)(F)C(O)=O>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([OH:25])=[O:24])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 12018742Ethyl 4-{3-methoxy-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoate

Produkt 1

HCID 101098274-{3-methoxy-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

The product of STEP 8 (67.5 mg, 0.17 mmol) was dissolved in 5 ml methanol and 5 ml 1N sodium hydroxide solution. The reaction was stirred at room temperature for 16 h, and acidified with trifluoroacetic acid (1.0 ml). Solvents were evaporated and residue was purified on HPLC using acetonitrile gradient 10-50% in 30 min to yield 31.5 mg. FAB-MS: (MH+)=373. H NMR(CDCl3) δ1.03 (s, 6H), 2.21 (p, 2H), 2.22 (s, 2H), 2.61 (s, 2H), 3.60 (q, 2H), 3.84 (s, 2H), 4.13 (t, 2H), 6.65-6.82 (m, 4H), 6.96 (d, 1H), 7.68-7.80 (m, 2H); Anal Calcd. for C21H28N2O4 plus 1.5 CF3COOH: C, 52.17; H, 5.56; N, 5.07. Found: C, 52.44; H, 5.62; N, 4.88.

Aufarbeitung

  1. customSolvents were evaporated
  2. customresidue was purified on HPLC
  3. customin 30 min
  4. customto yield 31.5 mg

Quellen und Nachweise

ORD-Eintrag
ord-f8b2596801664b6dbf0ab6e542a0bf00
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531494B1

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