Triethylamine → (R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-6-(3-nitro-benzenesulfonylamino)-hexanoic acid methyl ester

HRID 885507노트

반응식

HRID 885507 반응식
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([F:18])=[C:13]([CH3:19])[CH:12]=1)[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].[N+:21]([C:24]1[CH:25]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([F:18])=[C:13]([CH3:19])[CH:12]=1)[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][S:30]([C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=1)(=[O:31])=[O:32]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 69169741(R)-6-Amino-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid methyl ester

생성물 1

HCID 69169788(R)-2-(4-Fluoro-3,5-dimethyl-phenylamino)-6-(3-nitro-benzenesulfonylamino)-hexanoic acid methyl ester수율 39%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R)-6-amino-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid methyl ester (0.200 g, 0.709 mmol) and 3-nitro-benzenesulfonyl chloride (0.157 g, 0.709 mmol) in 10 mL of dichloromethane, was added triethylamine (0.5 mL, 3.544 mmol). After stirring at room temperature under N2 for 16 h, the reaction mixture was concentrated under reduced pressure. The product was isolated by Flash chromatography (silica gel) eluting with 20-50% ethyl acetate/hexanes to give the title compound as light yellow semi-solid (0.128 g, 39% yield). LC-MS: tR=9.5 min; m/z 468 (M+H)+.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe product was isolated by Flash chromatography (silica gel)
  3. washeluting with 20-50% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-7cf43ab67f7b41228c6e263f8fc4d602
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242174B2

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