Citric Acid → HCID 66926364, Verbindung

HRID 2404099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404099
[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH:3]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([CH:23]=O)[CH:17]=[CH:16]3)[CH2:2]1.[NH2:25][CH2:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].C(O)C.C([BH3-])#N.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[F:31][C:27]([F:32])([CH2:26][NH:25][CH2:23][C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([O:12][CH:3]3[CH2:2][CH2:1][C:6]4([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]4)[CH2:5][CH2:4]3)[CH:14]=2)[CH:19]=1)[C:28]([OH:30])=[O:29]

Komponenten

6

Edukt 5

HCID 311Citric AcidHCID 702EthanolHCID 27564053-Amino-2,2-difluoropropanoic acidHCID 5003444Sodium cyanoborohydrideHCID 86668414HCID 86668414, Verbindung

Produkt 1

HCID 66926364HCID 66926364, VerbindungAusbeute 41,4 %

Versuchsvorschrift

A solution of 6-(spiro[5.5]undec-3-yloxy)-naphthalene-2-carbaldehyde (150 mg, 0.46 mmol) and 3-amino-2,2-difluoro-propionic acid (58.2 mg, 0.465 mmol) in ethanol (0.7 mL, 10 mmol) was heated to reflux for 2 h. The yellow solution was then cooled to room temperature and sodium cyanoborohydride (35.1 mg, 0.558 mmol) was added portionwise. The resulting mixture was heated to reflux for 1 h. The reaction was then cooled to room temperature, and citric acid was added. The solution was stirred for several minutes and the solvent removed under vacuum. The resulting solid was suspended in water and filtered, and the collected solid was washed thoroughly with water (4×), ether (5×), and hexane (5×) to give (82.1 mg, 41%) of 2,2-difluoro-3-((6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)methylamino)propanoic acid. 1H NMR (400 MHz, CDCl3) δ: 7.93 (s, 1H), 7.86 (d, J=8.5 Hz, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.52 (dd, J=8.4, 1.8 Hz, 1H), 7.30 (d, J=2.2 Hz, 1H), 7.22 (dd, J=9.0, 2.4 Hz, 1H), 4.52 (m, 1H), 4.45 (s, 2H), 3.60 (t, J=15.9 Hz, 2H), 1.76-1.35 (m, 18H).

Aufarbeitung

  1. temperatureto reflux for 2 h
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 1 h
  4. temperatureThe reaction was then cooled to room temperature
  5. customthe solvent removed under vacuum
  6. filtrationfiltered
  7. washthe collected solid was washed thoroughly with water (4×), ether (5×), and hexane (5×)

Quellen und Nachweise

ORD-Eintrag
ord-2088a64912f64462991973ee476692f8
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802659B2

Notizen zur Reaktion

Wird geladen…