Acetone → N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

HRID 609576노트

반응식

HRID 609576 반응식
O=C1C2(CCNCC2)C(=O)CC1.O1[C:17]2([CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]4=[O:39])=[CH:25][C:24]=3[F:40])[CH2:19][CH2:18]2)[O:16]CC1.CC(C)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[F:40][C:24]1[CH:25]=[C:26]([N:29]2[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]2=[O:39])[CH:27]=[CH:28][C:23]=1[N:20]1[CH2:21][CH2:22][C:17](=[O:16])[CH2:18][CH2:19]1

참가 물질

6

반응물 4

HCID 180AcetoneHCID 2880631,4-Dioxo-8-azaspiro[4,5]decaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 9952477(S)-N-{3-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

생성물 1

HCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Using a commercially available 1,4-dioxo-8-aza-spiro[4.5]decane, (S)-N-{3-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}- acetamide is synthesized by the same method as in Step 1. To an acetone solution (70 ml) of this compound (3.79 g), water (20 ml) and p-toluenesulfonic acid monohydrate (3.66 g) are added successively and the mixture is heated under reflux for 3 hours. After the reaction mixture is cooled to room temperature, acetone is distilled off and the aqueous layer is neutralized with triethylamine. The solution is extracted with methylene chloride and the organic layer is washed with brine, dried over anhydrous sodium sulfate. The solvent is evaporated and the residue is purified by silica gel column chromatography (solvent: chloroform/methanol=50/1-25/1) to afford the title compound.

후처리

  1. customis synthesized by the same method as in Step 1
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 3 hours
  4. distillationacetone is distilled off
  5. extractionThe solution is extracted with methylene chloride
  6. washthe organic layer is washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent is evaporated
  9. customthe residue is purified by silica gel column chromatography (solvent: chloroform/methanol=50/1-25/1)

출처 및 근거

ORD 기록
ord-e8657d2588d64e309c6250919b260b10
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998406

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