Triethylamine → Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

HRID 242007

반응식

HRID 242007 반응식
[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(NC1C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1)(=O)C>C(#N)C>[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8](=[O:15])[C:9](=[N+:37]=[N-:38])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 51291854-Acetamidobenzenesulfonyl azideHCID 64717392Ethyl 3-(3-chloro-2-fluorophenyl)-3-oxopropanoate

생성물 1

HCID 86659989Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Ethyl 3-(3-chloro-2-fluorophenyl)-3-oxopropanoate (1.30 g, 5.31 mmol), triethylamine (0.618 g, 6.11 mmol, 1.15 equiv), and 4-acetamidobenzenesulfonyl azide (1.40 g, 5.85 mmol, 1.1 equiv) were combined in acetonitrile (15 mL). After stirred at ambient temperature for 30 minutes, the mixture was concentrated in vacuo and the residue was treated with sodium hydroxide (25 mL, 2 M aqueous) and extracted with twice chloroform. The combined organic extracts were washed once with brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 40:60; hexanes:ethyl acetate), providing the titled compound.

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. additionthe residue was treated with sodium hydroxide (25 mL, 2 M aqueous)
  3. extractionextracted with twice chloroform
  4. washThe combined organic extracts were washed once with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 40:60; hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-85b62a5695854a139211369c4df8ff2b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653079B2

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