Tributylphosphine → 3-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl-oxymethyl)oxazolidin-2-one

HRID 1167431ノート

反応式

HRID 1167431 の反応式
[Si:1]([O:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][OH:25])[O:21][C:20]3=[O:26])=[CH:15][C:14]=2[F:27])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[C:29]1[CH:33]=[CH:32][O:31][N:30]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Si:1]([O:8][CH:9]1[CH2:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][O:25][C:29]4[CH:33]=[CH:32][O:31][N:30]=4)[O:21][C:20]3=[O:26])=[CH:15][C:14]=2[F:27])[CH2:12]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 213565963-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-oneHCID 178516613HCID 178516613、化合物

生成物 1

HCID 699815973-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl-oxymethyl)oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (WO 96/13502; 2.47 g, 6.25 mmol), 3-hydroxyisoxazole (580 mg, 6.86 mmol), and tributylphosphine (1.58 g, 7.8 mmol) were dissolved by stirring in dry tetrahydrofuran (100 ml) under nitrogen. The mixture was cooled in an ice-bath, and 1,1′-(azodicarbonyl)dipiperidine (1.96 g, 7.8 mmol) added dropwise over 10 minutes. The solution was stirred 18 hours, allowing the temperature to rise to ambient. Reduced azo compound was filtered off, and the solution evaporated to dryness and the residue triturated with ether. The residue was purified by chromatography on a silica flash column, eluting with a gradient from 50 to 75% EtOAc in isohexane. Relevant fractions were combined and evaporated to the product as an oil (1.31 g).

後処理

  1. temperatureThe mixture was cooled in an ice-bath
  2. filtrationReduced azo compound was filtered off
  3. customthe solution evaporated to dryness
  4. customthe residue triturated with ether
  5. customThe residue was purified by chromatography on a silica flash column
  6. washeluting with a gradient from 50 to 75% EtOAc in isohexane
  7. customevaporated to the product as an oil (1.31 g)

出典と根拠

ORDレコード
ord-f888938a6a9e4456a370a053d7a26fed
出典データセット
uspto-grants-2003_09
特許番号
US06617339B1

反応ノート

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