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Ammonium Chloride → tert-Butyl {2-(dimethylsulphamoyl)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 220663
ノート
印刷プレビュー

反応式

HRID 220663 の反応式
[CH3:1][N:2]([CH3:7])[S:3]([CH3:6])(=[O:5])=[O:4].C([Li])CCC.[F:13][C:14]([F:31])([F:30])[C:15]1[CH:16]=[C:17](/[CH:21]=[N:22]/[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:18]=[CH:19][CH:20]=1.[Cl-].[NH4+]>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:1][N:2]([CH3:7])[S:3]([CH2:6][CH:21]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:31])([F:30])[F:13])[CH:16]=1)(=[O:5])=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 70191N,N-DimethylmethanesulphonamideHCID 46855703tert-butyl (NE)-N-[[3-(trifluoromethyl)phenyl]methylidene]carbamateHCID 178418339Butyllithium

生成物 1

HCID 59536741tert-Butyl {2-(dimethylsulphamoyl)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

試薬・触媒・溶媒 3

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8058Hexane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

A solution of 676 mg (5.49 mmol) of N,N-dimethylmethanesulphonamide in 10 ml of THF was admixed slowly at −78° C. with 3.43 ml (5.49 mmol) of 1.6M n-butyllithium solution in hexane versetzt. After 30 min at −78° C., the colourless solution obtained was added to a solution, cooled to −78° C. beforehand, of 500 mg (1.83 mmol) of the compound from Example 11A in 10 ml of THF. The reaction mixture was stirred at −78° C. for 30 min more and then slowly warmed to RT. After 30 min it was cooled to −20° C. again and the reaction was halted by addition of 5 ml of 10% strength aqueous ammonium chloride solution. The mixture was diluted with ethyl acetate and then washed twice with water and once with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate and freed from the solvent on a rotary evaporator. The residue was purified by preparative HPLC [Method 23]. The product fraction was freed from the solvent on a rotary evaporator. Drying of the residue in an HV gave 296 mg (41% of theory) of the title compound.

後処理

  1. customthe colourless solution obtained
  2. additionwas added to a solution
  3. temperatureslowly warmed to RT
  4. temperatureAfter 30 min it was cooled to −20° C. again
  5. washwashed twice with water and once with saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customfreed from the solvent on a rotary evaporator
  8. customThe residue was purified by preparative HPLC [Method 23]
  9. customThe product fraction was freed from the solvent on a rotary evaporator
  10. customDrying of the residue in an HV

出典と根拠

ORDレコード
ord-2ae4fdf9fcc54154850a5c8673581c0b
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202895B2

反応ノート

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