Trifluoroacetic acid → HCID 178472361、化合物

HRID 928116ノート

反応式

HRID 928116 の反応式
[Br:1][C:2]1[S:6][C:5]([C:7]2([C@H:10]3[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]3)[CH2:9][O:8]2)=[N:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([CH:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][OH:8])=[N:4][CH:3]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178472329HCID 178472329、化合物

生成物 1

HCID 178472361HCID 178472361、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution in DCM (0.7 mL) of ethyl trans-4-[2-(5-bromo-1,3-thiazol-2-yl)oxiran-2-yl]cyclohexanecarboxylate (30 mg, 0.082 mmol) from Step 2 was treated with trifluoroacetic acid (0.266 mL, 1.665 mmol) and triethylsilane (0.128 mL, 1.665 mmol) and left at 45° C. 16 h. The volatiles were removed under reduced pressure and the residue was taken up in dichloromethane, washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-2-hydroxyethyl]cyclohexanecarboxylate which was used as such without further characterization. MS ESI calc'd. for C14H20BrNO3S [M+H]+ 362, 364, found 362, 364.

後処理

  1. waitleft at 45° C
  2. custom16 h
  3. customThe volatiles were removed under reduced pressure
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-823ca7f188f041e3af218088e6678582
出典データセット
uspto-grants-2016_03
特許番号
US09290490B2

反応ノート

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