Citric Acid → HCID 66926364、化合物

HRID 2404099ノート

反応式

HRID 2404099 の反応式
[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]

参加物

6

反応物 5

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

生成物 1

HCID 66926364HCID 66926364、化合物収率 41.4%

実験手順

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).

後処理

  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×)

出典と根拠

ORDレコード
ord-2088a64912f64462991973ee476692f8
出典データセット
uspto-grants-2014_08
特許番号
US08802659B2

反応ノート

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