D-1,4-Dithiothreitol → Dimethyl-sulfamic acid 5-tert-butyl-4-mercapto-2-methyl-phenyl ester

HRID 1003865ノート

反応式

HRID 1003865 の反応式
[C:1]([C:5]1[C:6]([S:19]C#N)=[CH:7][C:8]([CH3:18])=[C:9]([O:11][S:12](=[O:17])(=[O:16])[N:13]([CH3:15])[CH3:14])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].SC[C@H]([C@@H](CS)O)O.OP([O-])(O)=O.[K+]>CCO>[C:1]([C:5]1[C:6]([SH:19])=[CH:7][C:8]([CH3:18])=[C:9]([O:11][S:12](=[O:16])(=[O:17])[N:13]([CH3:14])[CH3:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 446094D-1,4-DithiothreitolHCID 516951Monobasic potassium phosphateHCID 10496539Dimethyl-sulfamic acid 5-tert-butyl-2-methyl-4-thiocyanato-phenyl ester

生成物 1

HCID 10662229Dimethyl-sulfamic acid 5-tert-butyl-4-mercapto-2-methyl-phenyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a round bottom flask equipped with a magnetic stirrer and condenser were added 1.1 g (3.3 mmol) of dimethyl-sulfamic acid 5-tert-butyl-2-methyl-4-thiocyanato-phenyl ester (prepared in Example SSS), dithiothreitol (1.29 g, 8.35 mmol), EtOH (40 mL), and 0.02 M KH2PO4 buffer solution (5 mL), respectively. The reaction was refluxed overnight. The mixture was then quenched with H2O (250 mL) and extracted with a 1:1 mixture of hexanes:Et2O. The organic layer was again washed with H2O and brine, dried (MgSO4) and concentrated. The residue was dried under high vacuum to yield the title compound. 1H NMR (CDCl3) δ 1.45 (s, 9 H), 2.25 (s, 3 H), 3.02 (s, 6 H), 3.57 (s, 1 H), 7.01 (s, 1 H), 7.28 (s, 1 H).

後処理

  1. customTo a round bottom flask equipped with a magnetic stirrer and condenser
  2. temperatureThe reaction was refluxed overnight
  3. customThe mixture was then quenched with H2O (250 mL)
  4. extractionextracted with a 1:1 mixture of hexanes
  5. washThe organic layer was again washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was dried under high vacuum

出典と根拠

ORDレコード
ord-1b1a3e2398be4d3290266b1c0588f14b
出典データセット
uspto-grants-2000_04
特許番号
US06046355

反応ノート

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