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4-Toluenesulfonyl chloride → HCID 86709661, 화합물

HRID 2285366
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HRID 2285366 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C@H:12]([NH:14][C:15]([C@@H:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:43])[C@@H:24]([NH:26][C:27](=[O:42])[C@@H:28]([NH:32][C:33](=[O:41])[C:34]([CH2:38][CH2:39]O)([CH3:37])[CH:35]=[CH2:36])[CH:29]([CH3:31])[CH3:30])[CH3:25])[NH:18]3)=[O:16])[CH3:13])=[N:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C@H:12]([NH:14][C:15]([C@@H:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:43])[C@@H:24]([NH:26][C:27](=[O:42])[C@@H:28]([N:32]4[CH2:36][CH2:35][C:34]([CH3:37])([CH:38]=[CH2:39])[C:33]4=[O:41])[CH:29]([CH3:31])[CH3:30])[CH3:25])[NH:18]3)=[O:16])[CH3:13])=[N:9]2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 73974-Toluenesulfonyl chloride2회HCID 86709659(S)-1-((S)-2-{(S)-2-[2-(2-Hydroxy-ethyl)-2-methyl-but-3-enoylamino]-3-methyl-butyrylamino}-propionyl)-hexahydro-pyridazine-3-carboxylic acid [(R)-1-(7-bromo-quinolin-2-yl)-ethyl]-amide

생성물 1

HCID 86709661HCID 86709661, 화합물수율 42.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매2회
HCID 6344Dichloromethane용매

실험 절차

A solution of (S)-1-((S)-2-{(S)-2-[2-(2-hydroxy-ethyl)-2-methyl-but-3-enoylamino]-3-methyl-butyrylamino}-propionyl)-hexahydro-pyridazine-3-carboxylic acid [(R)-1-(7-bromo-quinolin-2-yl)-ethyl]-amide (186.4 mg, 0.282 mmol) and 4-dimethylaminopyridine (206.7 mg, 1.692 mmol) in dichloromethane (20 mL) was treated with para-toluenesulfonyl chloride (161.6 mg, 0.848 mmol). After stirring at room temperature for 2.5 h, more 4-dimethylaminopyridine (206.7 mg, 1.692 mmol) and para-toluenesulfonyl chloride (161.6 mg, 0.848 mmol) were added. After stirring at room temperature for 1.5 h, the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 20 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/acetone 1:0 to 3:2 to afford the title compound (77.0 mg, 42%) as a colourless gum and as a 1:1 mixture of diastereoisomers. LCMS (m/z) 643.1 [M+H], Tr=1.90 min and LCMS (m/z) 643.1 [M+H], Tr=1.99 min.

후처리

  1. stirringAfter stirring at room temperature for 1.5 h
  2. customthe volatiles were removed in vacuo
  3. customThe residue was purified by silica gel chromatography
  4. washeluted with a continuous gradient of iso-hexanes/acetone 1:0 to 3:2

출처 및 근거

ORD 기록
ord-9b196e2be4f842e2b2177c870da0c130
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145441B2

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