Triethylamine → (S)-4-Benzyl-3-((2S,3R)-3-hydroxy-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one

HRID 479122

反応式

HRID 479122 の反応式
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:18])[CH2:15][O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.B(OS(C(F)(F)F)(=O)=O)(CCCC)CCCC.[CH3:43][C:44]1[O:48][C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[N:46][C:45]=1[CH2:55][CH2:56][O:57][C:58]1[C:66]2[CH:65]=[CH:64][S:63][C:62]=2[C:61]([CH:67]=[O:68])=[CH:60][CH:59]=1>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:18])[C@@H:15]([O:16][CH3:17])[C@H:67]([OH:68])[C:61]1[C:62]2[S:63][CH:64]=[CH:65][C:66]=2[C:58]([O:57][CH2:56][CH2:55][C:45]2[N:46]=[C:47]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[O:48][C:44]=2[CH3:43])=[CH:59][CH:60]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2724243Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acidHCID 10106101(S)-4-benzyl-3-(2-methoxyacetyl)oxazolidin-2-oneHCID 111759364-[2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-1-benzothiophene-7-carbaldehyde

生成物 1

HCID 11387920(S)-4-Benzyl-3-((2S,3R)-3-hydroxy-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

0.249 g of (S)-4-Benzyl-3-methoxyacetyl-oxazolidin-2-one (1.00 mmol) was dissolved under an argon atmosphere in 2.5 ml of abs. CH2Cl2 and treated with 0.167 ml of triethylamine (1.2 eq.). After cooling to −78°, nBu2BOTf was added slowly (1.1 ml of 1M solution in CH2Cl2) and enolborinate formation allowed to proceed for 50 Min. at −78° and for 50 Min. at 0°. After recooling, a solution of 0.363 g of 4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-7-carbaldehyde (1.0 mmol) in 3.5 ml of abs. CH2Cl2 was added via dropping funnel and the mixture kept for 30 Min. at −78° and for 60 Min. at 0°. Pouring onto crashed ice, twofold extraction with AcOEt, washing with brine and water, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=7/3) left finally 0.259 g of the title compound as light yellow foam. According to NMR, one of the four isomers is strongly predominating. The configuration was tentatively assigned as 2S, 3R according to Tetrahedron Asymmetry 1999, 1353.

後処理

  1. temperatureAfter cooling to −78°
  2. customat −78°
  3. customat 0°
  4. customat −78°
  5. customat 0°
  6. additionPouring
  7. extractionice, twofold extraction with AcOEt
  8. washwashing with brine and water
  9. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  10. waitleft finally 0.259 g of the title compound as light yellow foam

出典と根拠

ORDレコード
ord-8d3352760e9d46a3b369734e53c6ae87
出典データセット
uspto-grants-2003_11
特許番号
US06642389B2

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