Diisopropylethylamine → tert-Butyl (1S)-1-(3-bromo-4-iodobenzyl)-2-oxo-2-[(2-oxo-2-phenylethyl)amino]ethylcarbamate

HRID 724723노트

반응식

HRID 724723 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[I:8].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[NH2:50][CH2:51][C:52]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:53].C(N(CC)C(C)C)(C)C>C(=O)(O)[O-].[Na+].CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[I:8])[CH2:9][C@H:10]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11](=[O:13])[NH:50][CH2:51][C:52](=[O:53])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 69597598(2S)-3-(3-bromo-4-iodophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

생성물 1

HCID 58746572tert-Butyl (1S)-1-(3-bromo-4-iodobenzyl)-2-oxo-2-[(2-oxo-2-phenylethyl)amino]ethylcarbamate수율 33.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of (2S)-3-(3-bromo-4-iodophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (4.10 g, 6.10 mmol), N,N-dimethylformamide (49 mL) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (4.24 g, 9.59 mmol) was stirred at 25° C. After stirring for 10 min, added 2-amino-1-phenylethanone hydrochloride (2.24 g, 13.1 mmol) and N,N-diisopropylethylamine (7.60 mL). The reaction was stirred at 25° C. for 2 h. The reaction was diluted with saturated sodium bicarbonate and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.2 g, 33%). MF=C22H24BrIN2O4; LCMS found for C22H25BrIN2O4 (M+H−Boc)+: m/z=487.

후처리

  1. stirringThe reaction was stirred at 25° C. for 2 h
  2. extractionextracted with ethyl acetate three times
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-f4f35f990acf460e80d8137118181220
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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