Diisopropylethylamine → (2R,4S)-4-((tert-Butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl 2-fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzenesulfonate

HRID 630613ノート

反応式

HRID 630613 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[NH:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[S:14](Cl)(=[O:16])=[O:15].[OH:18][CH2:19][C@:20]([OH:37])([CH3:36])[C:21](=[O:35])[C@@H:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:23][CH:24]([CH3:26])[CH3:25].CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[NH:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[S:14]([O:18][CH2:19][C@:20]([OH:37])([CH3:36])[C:21](=[O:35])[C@@H:22]([NH:27][C:28]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:34])[CH2:23][CH:24]([CH3:26])[CH3:25])(=[O:15])=[O:16]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 867153592-Fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzene-1-sulfonyl chlorideHCID 86715361tert-butyl ((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)carbamate

生成物 1

HCID 86715360(2R,4S)-4-((tert-Butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl 2-fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzenesulfonate収率 75%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

2-Fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzene-1-sulfonyl chloride (3, 2.52 g, 9.14 mmol) was added dropwise to tert-butyl ((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)carbamate (2.65 g, 9.14 mmol), DIEA (1.91 mL, 10 mmol) and DMAP (0.1 g, 0.914 mmol) in DCM (30 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The reaction was washed with 2N HCl and brine, dried (MgSO4) and evaporated. The residue was purified by Biotage flash column chromatography (30% EtOAc/Hep) to give product as an oil (3.62 g, 75%).

後処理

  1. washThe reaction was washed with 2N HCl and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by Biotage flash column chromatography (30% EtOAc/Hep)

出典と根拠

ORDレコード
ord-be240d9a76ee4d6fabae9844d2ee9d71
出典データセット
uspto-grants-2016_04
特許番号
US09315542B2

反応ノート

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