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Ammonium Chloride → 1-(4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}phenyl)ethanol

HRID 909498
ノート
印刷プレビュー

反応式

HRID 909498 の反応式
[CH3:1][O:2][CH2:3][C@H:4]([CH3:32])[O:5][C:6]1[CH:7]=[C:8]([CH:19]=[C:20]([C:22]2[NH:23][C:24]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[CH:25][CH:26]=2)[CH:21]=1)[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1.[BH4-].[Na+].[Cl-].[NH4+]>O1CCCC1.CO>[CH3:1][O:2][CH2:3][C@H:4]([CH3:32])[O:5][C:6]1[CH:7]=[C:8]([CH:19]=[C:20]([C:22]2[NH:23][C:24]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[CH:25][CH:26]=2)[CH:21]=1)[O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:18])[CH3:17])=[CH:12][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 580654701-(4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}phenyl)ethanone

生成物 1

HCID 580654671-(4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}phenyl)ethanol収率 91.1%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

1-(4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}phenyl)ethanone (30 mg, 0.067 mmol) synthesized in Example (39b) was dissolved in a mixed solvent of tetrahydrofuran (3.0 mL) and methanol (1.0 mL), and sodium borohydride (10 mg, 0.264 mmol) was added, followed by stirring at room temperature for 3 hours under nitrogen atmosphere. To this reaction solution, a saturated aqueous ammonium chloride solution (10 mL) was added, and extraction was carried out with ethyl acetate (10 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-60%) to afford the desired compound (27.5 mg, yield 91%) as a white solid.

後処理

  1. additionwas added
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified
  7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-60%)

出典と根拠

ORDレコード
ord-6f00cb0040a54e5f8c7f2f09bbb08d89
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017610B2

反応ノート

読み込み中…

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