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 1452594ノート

反応式

HRID 1452594 の反応式
[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

参加物

5

反応物 3

HCID 5363146Diisopropyl azodicarboxylateHCID 86598351HCID 86598351、化合物HCID 178438076HCID 178438076、化合物

生成物 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-one収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c4aef61e8e6e42e0b701856ea455e4ab
出典データセット
uspto-grants-2009_01
特許番号
US07473699B2

反応ノート

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