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Isopropyl Acetate → (4-{[4-(Fluoromethyl)piperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)boronic acid

HRID 473896
ノート
印刷プレビュー

反応式

HRID 473896 の反応式
Cl.[O:2]1[C:8]2[CH:9]=[CH:10][C:11]([B:13]([OH:15])[OH:14])=[CH:12][C:7]=2[CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+].[F:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29](Cl)=[O:30])[CH2:25][CH2:24]1.C(OC(C)C)(=O)C>C1COCC1>[F:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([N:5]2[CH2:6][C:7]3[CH:12]=[C:11]([B:13]([OH:15])[OH:14])[CH:10]=[CH:9][C:8]=3[O:2][CH2:3][CH2:4]2)=[O:30])[CH2:25][CH2:24]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 4

HCID 7915Isopropyl AcetateHCID 516892Sodium BicarbonateHCID 66820605(2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepin-7-yl)boronic acid hydrochlorideHCID 866720264-(Fluoromethyl)piperidine-1-carbonyl chloride

生成物 1

HCID 67514561(4-{[4-(Fluoromethyl)piperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)boronic acid収率 52%

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2,3,4,5-tetrahydro-1,4-benzoxazepin-7-ylboronic acid hydrochloride salt (188 mg, 0.82 mmol) was taken into 50% aqueous THF (2 mL) followed by addition of solid sodium bicarbonate (360 mg, 4.3 mmol) then 4-(fluoromethyl)piperidine-1-carbonyl chloride (reagent preparation 37) (218 mg, 1.21 mmol) in a minimum of THF. The mixture was stirred at room temperature over 1 h then partitioned with 0.5M aqueous hydrochloric acid and ethyl acetate. The organic solution was then brine washed, dried over anhydrous sodium sulfate, filtered and concentrated. The residue obtained was taken into isopropyl acetate and extracted once with 1M aqueous sodium hydroxide. The aqueous solution was then acidified to pH 2 using concentrated hydrochloric acid and extracted once with ethyl acetate then brine washed, dried over anhydrous sodium sulfate, filtered and concentrated to provide (4-{[4-(fluoromethyl)piperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)boronic acid (143 mg, 52% yield) as an amorphous residue. MS (EI) for C16H22BrFN2O4: 337 (MH+).

後処理

  1. customthen partitioned with 0.5M aqueous hydrochloric acid and ethyl acetate
  2. washbrine washed
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue obtained
  7. extractionextracted once with 1M aqueous sodium hydroxide
  8. extractionextracted once with ethyl acetate
  9. washbrine washed
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-f1b261545802427c89a0fa664261c838
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637499B2

反応ノート

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