Diisopropylcarbodiimide → D-tryptophanamide

HRID 337241

반응식

HRID 337241 반응식
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

참가 물질

5

반응물 3

HCID 12734DiisopropylcarbodiimideHCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophanHCID 178515910HCID 178515910, 화합물

생성물 1

HCID 688582D-tryptophanamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c19c3dcd1aab472d82f4ae4e6da344fe
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889723B2

연결된 노트

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