Diisopropyl azodicarboxylate → (5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[(5-Ethyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one

HRID 1452594노트

반응식

HRID 1452594 반응식
[CH2:1]([C:3]1[NH:7][N:6]=[N:5][N:4]=1)[CH3:2].N([CH2:11][C@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[C:22]([F:24])[C:21]([C:25]3[CH2:26][CH2:27][S:28](=[O:32])(=[O:31])[CH2:29][CH:30]=3)=[C:20]([F:33])[CH:19]=2)[CH2:13]1)=[N+]=[N-].CC(OC(/N=N/C(OC(C)C)=O)=O)C>ClCCl>[O:32]=[S:28]1(=[O:31])[CH2:27][CH:26]=[C:25]([C:21]2[C:22]([F:24])=[CH:23][C:18]([N:14]3[CH2:13][C@H:12]([CH2:11][N:5]4[N:6]=[N:7][C:3]([CH2:1][CH3:2])=[N:4]4)[O:16][C:15]3=[O:17])=[CH:19][C:20]=2[F:33])[CH2:30][CH2:29]1

참가 물질

5

반응물 3

HCID 5363146Diisopropyl azodicarboxylateHCID 86598351HCID 86598351, 화합물HCID 178438076HCID 178438076, 화합물

생성물 1

HCID 10048818(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-[(5-Ethyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Ethyl-1H-tetrazole (0.164 g, 1.67 mmol), (5R)-3-[4-(1,1-dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(hydroxymethyl)oxazolidin-2-one (WO 01/81350 A1) (0.30 g, 0.84 mmol), and polystyrene-triphenylphosphine (1.73 mmol/g loading: Argonaut Technologies, Inc. Foster City, Calif. USA, 1.46 g, 2.53 mmol) were dissolved in dry dichloromethane (30 ml). Diisopropylazodicarboxylate (0.33 ml, 1.68 mmol) was added and the mixture was stirred at room temperature for 16 hours. The resin was filtered off and rinsed with dichloromethane. The filtrate was evaporated to dryness and purified by chromatography on silica gel with 10% acetonitrile in dichloromethane. The material obtained after chromatography was precipitated from dichloromethane with diethyl ether to yield the title compound as a white powder (0.26 g, 71%).

후처리

  1. filtrationThe resin was filtered off
  2. washrinsed with dichloromethane
  3. customThe filtrate was evaporated to dryness
  4. custompurified by chromatography on silica gel with 10% acetonitrile in dichloromethane
  5. customThe material obtained after chromatography
  6. customwas precipitated from dichloromethane with diethyl ether

출처 및 근거

ORD 기록
ord-c4aef61e8e6e42e0b701856ea455e4ab
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473699B2

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