Diisopropylcarbodiimide → D-tryptophanamide

HRID 337241

反応式

HRID 337241 の反応式
C([NH:8][C@@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(OC(C)(C)C)=O.[NH4+].OC1C2N=N[NH:30]C=2C=CC=1.C(N=C=NC(C)C)(C)C>CN(C)C=O>[NH2:8][C@@H:9]([C:20]([NH2:30])=[O:22])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1

参加物

5

反応物 3

HCID 12734DiisopropylcarbodiimideHCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophanHCID 178515910HCID 178515910、化合物

生成物 1

HCID 688582D-tryptophanamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-Boc-D-Tryptophan (9) (1 equiv.; 2.75 mmol; 1.00 g), hydroxybenzotriazole ammonium salt (2 equiv.; 5.50 mmol; 924 mg) and diisopropylcarbodiimide (DIC) (1.1 equiv.; 3.03 mmol; 382 mg; 454 μl) were dissolved in dimethylformamide (DMF) which had been dried over molecular sieves, and the solution was stirred at room temperature for 18 h. The solvent was then removed on a rotary evaporator under reduced pressure, and the residue was taken up in ethyl acetate. Insoluble residues were filtered off, and the organic phase was then washed (1×1 M KHSO4 solution, 2× saturated aqueous sodium carbonate solution, 1× saturated aqueous sodium chloride solution), dried over sodium sulfate and evaporated.

後処理

  1. customhad been dried over molecular sieves
  2. customThe solvent was then removed on a rotary evaporator under reduced pressure
  3. filtrationInsoluble residues were filtered off
  4. washthe organic phase was then washed (1×1 M KHSO4 solution, 2× saturated aqueous sodium carbonate solution, 1× saturated aqueous sodium chloride solution)
  5. dry with materialdried over sodium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-c19c3dcd1aab472d82f4ae4e6da344fe
出典データセット
uspto-grants-2014_11
特許番号
US08889723B2

関連ノート

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