Citric Acid → HCID 66926364, 화합물

HRID 713880노트

반응식

HRID 713880 반응식
[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]

참가 물질

6

반응물 5

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

생성물 1

HCID 66926364HCID 66926364, 화합물수율 41.4%

실험 절차

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).

후처리

  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×)

출처 및 근거

ORD 기록
ord-85b86c902df94169962220b40c98e14c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186367B2

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