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Acetic Acid → [4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde

HRID 1867352
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HRID 1867352 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10](/[CH:15]=[CH:16]/[C:17]([N:19]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]([CH2:27][C:28](N(OC)C)=[O:29])[CH2:21][CH2:20]2)=[O:18])[CH:11]=[CH:12][C:13]=1[Cl:14].CC(C)=O.C(O)(=O)C.OS([O-])(=O)=O.[K+]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10](/[CH:15]=[CH:16]/[C:17]([N:19]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]([CH2:27][CH:28]=[O:29])[CH2:21][CH2:20]2)=[O:18])[CH:11]=[CH:12][C:13]=1[Cl:14]
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참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 180AcetoneHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 866158622-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-N-methoxy-N-methyl-acetamide

생성물 1

HCID 86615863[4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde
수율 75.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-30 °C

실험 절차

7.92 ml (7.92 mmol) of a LAH-solution (1.0 M in THF) was dropped to a cooled (−30° C.) suspension of 3.28 g (7.92 mmol) of 2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-N-methoxy-N-methyl-acetamide in 260 ml of THF. The reaction was stirred for 5 min at −30° C. and then cooled to −78° C. The reaction was stopped by adding first 12.8 ml (174.24 mmol) of acetone and afterwards 0.9 mL (15.84 mmol) of acetic acid. The reaction was then powered to an aqueous 10% KHSO4 solution and extracted with ether (3×), the organic phase was dried over Na2SO4 evaporated dissolved in toluene and evaporated (3×) to yield 2.12 g (75%) of the title compound as light yellow foam. MS: 355.0 (MH+, 2Cl).

후처리

  1. temperaturea cooled
  2. temperaturecooled to −78° C
  3. extractionextracted with ether (3×)
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated
  6. dissolutiondissolved in toluene
  7. customevaporated (3×)

출처 및 근거

ORD 기록
ord-aee5e64afe87435c86761fa4f4016760
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07632829B2

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