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Dimethylformamide → 4,5-Difluoro-3-(3,5-dimethylphenylsulphonyl) indole 2-carboxyserinamide

HRID 902176
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인쇄 미리보기

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HRID 902176 반응식
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([S:15]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=1)(=[O:17])=[O:16])=[C:5]([C:12](O)=[O:13])[NH:6]2.Cl.[NH2:27][C@H:28]([C:31]([NH2:33])=[O:32])[CH2:29][OH:30].C(N(CC)CC)C.CN(C)C=[O:44]>O>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([S:15]([C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1)(=[O:17])=[O:16])=[CH:5][NH:6]2.[C:29]([C@@:28]([C:31]([NH2:33])=[O:32])([CH2:12][OH:13])[NH2:27])([OH:44])=[O:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 16212403L-Serinamide hydrochlorideHCID 213010464,5-Difluoro-3-(3,5-dimethylphenylsulphonyl)indole 2-carboxylic acid

생성물 1

HCID 690293034,5-Difluoro-3-(3,5-dimethylphenylsulphonyl) indole 2-carboxyserinamide수율 97.9%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

4,5-Difluoro-3-(3,5-dimethylphenylsulphonyl)indole 2-carboxylic acid (3.52 g) and L-serinamide hydrochloride (2.77 g) were dissolved in anhydrous dimethylformamide (90 ml). Triethylamine (2.8 ml) was added and the mixture stirred for 5 minutes. Benzotriazol-1-yloxy-tris(dimethylamino)phosphosphonium hexafluorophosphate (BOP) (4.69 g) was added and the orange mixture was stirred overnight at room temperature. The reaction mixture was diluted with water (350 ml) and the white solid precipitate collected by filtration, washed with water and dried to afford the title product (3.86 g) as a white powder (97.9% pure by hplc).

후처리

  1. stirringthe orange mixture was stirred overnight at room temperature
  2. filtrationthe white solid precipitate collected by filtration
  3. washwashed with water
  4. customdried

출처 및 근거

ORD 기록
ord-d86e541ad6b84fa4905d7022efd896e1
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07365090B2

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