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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
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HRID 558983 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-24c63e0341914c05ad86e49d3b5d1f40
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063038B2

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