Sodium Bicarbonate → 3[2-(1(S)-Hydroxy-3-cyanopropyl)benzothiazol-6-yl]-5(R)-methoxymethyl-2-oxazolidinone

HRID 2259652ノート

反応式

HRID 2259652 の反応式
[OH:1][CH:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][CH:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH:4]=NO.FC(F)(F)C([C:29]1[NH:30]C=CN=1)=O.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:1][C@H:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][C@H:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH2:4][C:29]#[N:30]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 5654362,2,2-Trifluoro-1-(1H-imidazol-2-yl)ethanoneHCID 73508098HCID 73508098、化合物

生成物 1

HCID 98846473[2-(1(S)-Hydroxy-3-cyanopropyl)benzothiazol-6-yl]-5(R)-methoxymethyl-2-oxazolidinone収率 70.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

73 g of the 3-[2-(1-hydroxy-3-hydroxyiminopropyl)benzothiazol-6-yl]-5-methoxymethyl-2 -oxazolidinone obtained in the Example 8 was dissolved in 800 ml of tetrahydrofuran. 90 g of trifluoroacetylimidazole was added dropwise to the solution under cooling with ice and the mixture was stirred at room temperature for 4 h. The reaction liquid was poured into an aqueous sodium hydrogencarbonate solution. After extraction with ethyl acetate followed by washing with an aqueous common salt solution, drying over magnesium sulfate and concentration under reduced pressure, the obtained solid was recrystallized from acetone/water to give 51 g of the titled compound.

後処理

  1. temperatureunder cooling with ice
  2. customThe reaction liquid
  3. extractionAfter extraction with ethyl acetate
  4. washby washing with an aqueous common salt solution
  5. dry with materialdrying over magnesium sulfate and concentration under reduced pressure
  6. customthe obtained solid was recrystallized from acetone/water

出典と根拠

ORDレコード
ord-504c034ea2b04ddcaeb496797fa0a37c
出典データセット
uspto-grants-1995_12
特許番号
US05475014

反応ノート

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