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Acetic Acid → 9-Fluoro-5-oxo-2,3,4,5-tetrahydrobenzo[e][1,4]diazepine-1-carboxylic acid tert-butyl ester

HRID 558983
ノート
印刷プレビュー

反応式

HRID 558983 の反応式
C(OC([NH:11][CH2:12][CH2:13][N:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:15]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18])=O)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[C:28]([O:27][C:25]([N:14]1[C:15]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:16]=2[C:17](=[O:18])[NH:11][CH2:12][CH2:13]1)=[O:26])([CH3:31])([CH3:30])[CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 176Acetic AcidHCID 670000432-[(2-Benzyloxycarbonylaminoethyl)-tert-butoxycarbonylamino]-3-fluorobenzoic acid

生成物 1

HCID 670000169-Fluoro-5-oxo-2,3,4,5-tetrahydrobenzo[e][1,4]diazepine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of 2-[(2-benzyloxycarbonylaminoethyl)-tert-butoxycarbonylamino]-3-fluorobenzoic acid from Example 20B (390 mg, 0.87 mmol), 10% palladium/carbon (˜100 mg) and acetic acid (1.0 ml) in methanol (25 ml) was hydrogenated at atmospheric pressure for 1.5 h. The mixture was filtered, evaporated in vacuo and azeotroped with toluene. The residue was taken up in a mixture of IPA and acetic acid (90:10, 35 ml) and heated at reflux for 4 h. The mixture was cooled, evaporated in vacuo and azeotroped with toluene to give a white solid; yield 250 mg, 100%.

後処理

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo
  3. customazeotroped with toluene
  4. additionThe residue was taken up in a mixture of IPA and acetic acid (90:10, 35 ml)
  5. temperatureheated
  6. temperatureat reflux for 4 h
  7. temperatureThe mixture was cooled
  8. customevaporated in vacuo
  9. customazeotroped with toluene
  10. customto give a white solid

出典と根拠

ORDレコード
ord-24c63e0341914c05ad86e49d3b5d1f40
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063038B2

反応ノート

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