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

HRID 885507ノート

反応式

HRID 885507 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-7cf43ab67f7b41228c6e263f8fc4d602
出典データセット
uspto-grants-2012_08
特許番号
US08242174B2

反応ノート

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