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Triethylamine → Setafrastat

HRID 710032
ノート
印刷プレビュー

反応式

HRID 710032 の反応式
[F:1][C:2]([F:17])([C:6]1([OH:16])[CH2:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:8]([CH3:15])([CH3:14])[CH2:7]1)[C:3]([OH:5])=O.CCN(CC)CC.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C:33]2[O:37][N:36]=[C:35]([C@@H:38]3[CH2:42][CH2:41][CH2:40][NH:39]3)[CH:34]=2)[CH:26]=1.C(=O)(O)[O-].[Na+]>C1COCC1.ClC(OCC)=O>[F:17][C:2]([F:1])([C:6]1([OH:16])[CH2:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:8]([CH3:15])([CH3:14])[CH2:7]1)[C:3]([N:39]1[CH2:40][CH2:41][CH2:42][C@H:38]1[C:35]1[CH:34]=[C:33]([CH2:32][O:31][C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)[O:37][N:36]=1)=[O:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 68542826Difluoro(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetic acidHCID 86706744(S)-5-((Pyridin-3-yloxy)methyl)-3-(pyrrolidin-2-yl)isoxazole

生成物 1

HCID 73672050Setafrastat収率 58.5%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 10928Ethyl chloroformate溶媒

実験手順

To a solution of 2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetic acid (3.192 g) and Et3N (4.44 mL) in THF (100 mL), ethyl chloroformate (1.12 mL) was added at room temperature and the mixture was stirred for an hour. To the reaction mixture, a THF (50 mL) solution of the compound (2.607 g) obtained in Example 2-(3) was added dropwise at room temperature and the mixture was stirred at room temperature for 64 hours. To the reaction mixture, saturated aqueous sodium bicarbonate (200 mL) was added and the organic layer extracted with AcOEt (200 mL) was washed with brine (200 mL), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by NH-form silica gel chromatography (AcOEt/hexane); the resulting compound was recrystallized (Et2O/pentane) to give the titled compound (2.969 g, colorless powder.)

後処理

  1. stirringthe mixture was stirred at room temperature for 64 hours
  2. extractionthe organic layer extracted with AcOEt (200 mL)
  3. washwas washed with brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas further purified by NH-form silica gel chromatography (AcOEt/hexane)
  9. customthe resulting compound was recrystallized (Et2O/pentane)

出典と根拠

ORDレコード
ord-d1482ff9c6944c54b53d738c9e260271
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181229B2

反応ノート

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