Dimethylformamide → O-{[(3-sulfophenyl)amino]carbonyl}-L-serine

HRID 330858ノート

反応式

HRID 330858 の反応式
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:5]([O:7]C(C)(C)C)=[O:6])[CH2:3][OH:4].N[C:20]1[CH:21]=[C:22]([S:26]([OH:29])(=[O:28])=[O:27])C=CC=1.CN(C=[O:34])C.C([N:38]([CH:41]([CH3:43])[CH3:42])[CH2:39]C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[S:26]([C:22]1[CH:43]=[C:41]([NH:38][C:39]([O:4][CH2:3][C@@H:2]([C:5]([OH:7])=[O:6])[NH2:1])=[O:34])[CH:42]=[CH:20][CH:21]=1)([OH:29])(=[O:28])=[O:27]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 84743-Aminobenzenesulfonic acidHCID 81531DiisopropylethylamineHCID 7019054Boc-Ser-Otbu

生成物 1

HCID 45275682O-{[(3-sulfophenyl)amino]carbonyl}-L-serine収率 0.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
0 °C

実験手順

Boc-Ser-OtBu (200 mg, 0.77 mmol) was dissolved in 3 ml of methylene chloride and cooled to 0° C. N,N′-Carbonyldiimidazole (124 mg, 0.77 mmol) was added to the solution and stirred at room temperature for 2 hours. After the solvent was removed by distillation, 3-aminobenzenesulfonic acid (132.6 mg, 0.77 mmol), 2 ml of DMF and 0.4 ml of diisopropylethylamine were added and stirred at 70° C. overnight. The solvent was removed by distillation and the mixture was purified according to the purification step A to give the intermediate. The resulting intermediate was dissolved in 1 ml of TFA and stirred at room temperature for 2 hours. The solvent was removed by distillation, and the mixture was purified according to the purification step A to give the title compound.

後処理

  1. additionwere added
  2. stirringstirred at 70° C. overnight
  3. customThe solvent was removed by distillation
  4. customthe mixture was purified
  5. customaccording to the purification step A
  6. customto give the intermediate
  7. stirringstirred at room temperature for 2 hours
  8. customThe solvent was removed by distillation
  9. customthe mixture was purified
  10. customaccording to the purification step A

出典と根拠

ORDレコード
ord-a494a03bbd9548e6be718b833d9176ee
出典データセット
uspto-grants-2014_11
特許番号
US08877739B2

反応ノート

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