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1-Hydroxybenzotriazole → Tert-butyl (4-{2-[2-(acetylamino)-5-({[4-(methylthio)benzyl]amino}carbonyl)-1,3-thiazol-4-yl]ethyl}phenyl)carbamate

HRID 2117900
ノート
印刷プレビュー

反応式

HRID 2117900 の反応式
[C:1]([NH:4][C:5]1[S:6][C:7]([C:26](O)=[O:27])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].[CH3:29][S:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:22]([O:21][C:19](=[O:20])[NH:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][C:8]2[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=2[C:26]([NH:36][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([S:30][CH3:29])=[CH:32][CH:33]=2)=[O:27])=[CH:13][CH:14]=1)([CH3:25])([CH3:24])[CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27600804-(Methylthio)benzylamineHCID 219153162-(Acetylamino)-4-(2-[4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-1,3-thiazole-5-carboxylic acid

生成物 1

HCID 86595599
Tert-butyl (4-{2-[2-(acetylamino)-5-({[4-(methylthio)benzyl]amino}carbonyl)-1,3-thiazol-4-yl]ethyl}phenyl)carbamate
収率 102.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-1,3-thiazole-5-carboxylic acid (120 mg), [4-(methylthio)benzyl]amine (45.4 mg), 1-hydroxybenzotriazole (44 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (59.6 mg) in DMF (2 ml) was stirred at r.t. for 17 hours. The reaction mixture was poured into saturated NaHCO3, and extracted with CHCl3. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by preparative silica gel chromatography with CHCl3/AcOEt (1:1) as an eluent to give tert-butyl(4-(2-[2-(acetylamino)-5-({[4-(methylthio)benzyl]amino}carbonyl)-1,3-thiazol-4-yl]ethyl}phenyl)carbamate (163.5 mg) as an off-white solid.

後処理

  1. extractionextracted with CHCl3
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative silica gel chromatography with CHCl3/AcOEt (1:1) as an eluent

出典と根拠

ORDレコード
ord-a33203d64549423c94545a245d810c30
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07442715B2

反応ノート

読み込み中…

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