Diethyl Ether → (S)-2-(Acetylthio)-3-cyclohexylpropanoic acid

HRID 1379672ノート

反応式

HRID 1379672 の反応式
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Br[C@H:7]([CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:8]([OH:10])=[O:9].C1(NC2CCCCC2)CCCCC1.CCOCC>C(#N)C>[C:1]([S:3][C@@H:7]([CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:8]([OH:10])=[O:9])(=[O:4])[CH3:2]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 7582DicyclohexylamineHCID 23670855Potassium ethanethioateHCID 54556403(2R)-2-bromo-3-cyclohexylpropanoic acid

生成物 1

HCID 53963220(S)-2-(Acetylthio)-3-cyclohexylpropanoic acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

To a stirred slurry of potassium thioacetate (1.07 g., 9.36 mmol.) in dry acetonitrile (15 ml.) at 0° C. under argon was added a solution of (R)-2-bromo-3-cyclohexylpropanoic acid (2.20 g., 9.36 mmol.) in acetonitrile (3 ml.) over 10 minutes. The reaction was warmed to room temperature and stirred 16 hours. The resulting slurry was filtered and evaporated. The residue was redissolved in ethyl acetate, washed once with 5% potassium bisulfate solution, dried (sodium sulfate) and evaporated. The oily yellow residue (2.21 g.) was dissolved in ether and treated with a solution of dicyclohexylamine (1.8 ml., 9.0 mmol.) in 5 ml. of ether. Scratching the flask surface with a glass rod provided 2.38 g. of white crystalline title product; m.p. 159°-161° C., [α]D =-41.2° (c=1.0, chloroform).

後処理

  1. filtrationThe resulting slurry was filtered
  2. customevaporated
  3. dissolutionThe residue was redissolved in ethyl acetate
  4. washwashed once with 5% potassium bisulfate solution
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. dissolutionThe oily yellow residue (2.21 g.) was dissolved in ether
  8. customprovided 2.38 g

出典と根拠

ORDレコード
ord-5dc437da867441db8d1dbf343bd71618
出典データセット
uspto-grants-1997_09
特許番号
US05672599

反応ノート

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