Trifluoroacetic acid → 3-methyl-4-{[(3R)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile

HRID 43376ノート

反応式

HRID 43376 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[C@H:14]([CH3:25])[CH2:13]2)(=[O:11])=[O:10])=[C:5]([CH3:26])[CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[CH3:26][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[S:9]([N:12]1[CH2:17][CH2:16][NH:15][C@H:14]([CH3:25])[CH2:13]1)(=[O:11])=[O:10])[C:1]#[N:2]

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 591613281,1-dimethylethyl (2R)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate

生成物 1

HCID 591613863-methyl-4-{[(3R)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile収率 95.7%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 1,1-dimethylethyl (2R)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate (may be prepared as described in Description 19) (3.24 g, 8.54 mmol) and TFA (7.00 ml, 91.0 mmol) in dry DCM (10 ml) was stirred at rt for 1 h, then concentrated under vacuum, azetroping with toluene (25 ml) to give an orange oil. This was redissolved in MeOH (10 ml) then applied to an SCX-2 cartridge (50 g), washing with MeOH. The product was eluted with 2M NH3 in MeOH; concentration under vacuum gave the title compound as a pale orange oil (8.17 mmol).

後処理

  1. concentrationconcentrated under vacuum
  2. customto give an orange oil
  3. washwashing with MeOH
  4. washThe product was eluted with 2M NH3 in MeOH
  5. concentrationconcentration under vacuum

出典と根拠

ORDレコード
ord-8157cc6e5a8a49629901a9b2620fa4c1
出典データセット
uspto-grants-2013_09
特許番号
US08536183B2

反応ノート

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