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

HRID 705449
ノート
印刷プレビュー

反応式

HRID 705449 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]
参加物反応条件実験手順後処理出典と根拠反応ノート

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 down to 0° C. N,N′-carbonyldiimidazole (124 mg, 0.77 mmol) was added thereto and stirred at room temperature for 2 hours. After removing a solvent, 3-aminobenzenesulfonic acid (132.6 mg, 0.77 mmol), 2 mL of DMF and 0.4 mL of diisopropylethylamine were added thereto and stirred at 70° C. overnight. After removing a solvent, the mixture was purified in accordance with the purification process A to obtain an intermediate. The obtained intermediate was dissolved in 1 mL of TFA and stirred at room temperature for 2 hours. After removing a solvent, purification was conducted in accordance with the purification process A to obtain a title compound.

後処理

  1. additionwere added
  2. stirringstirred at 70° C. overnight
  3. customAfter removing a solvent
  4. customthe mixture was purified in accordance with the purification process
  5. customA to obtain an intermediate
  6. stirringstirred at room temperature for 2 hours
  7. customAfter removing
  8. customa solvent, purification

出典と根拠

ORDレコード
ord-acb1354df1474281a1e3ac071f222f3f
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174932B2

反応ノート

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