Diisopropylethylamine → Rac-4-(2-iodo-5-methanesulfonyl-benzoyl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 32737ノート

反応式

HRID 32737 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:15][C:16]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:17]=1[C:18](O)=[O:19].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:18](=[O:19])[C:17]2[CH:21]=[C:22]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:23]=[CH:24][C:16]=2[I:15])[CH:10]([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylateHCID 574452812-Iodo-5-methanesulfonyl-benzoic acid

生成物 1

HCID 59793735Rac-4-(2-iodo-5-methanesulfonyl-benzoyl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester収率 47.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of rac-3-Methyl-piperazine-1-carboxylic acid tert-butyl ester (350 mg, 1.75 mmol) in dimethylformamide (3 ml) were added 2-Iodo-5-methanesulfonyl-benzoic acid (540 mg, 1.67 mmol), N-ethyldiisopropylamine (1.8 ml, 10.5 mmol), and TBTU (630 mg, 1.92 mmol). The reaction mixture was then allowed to stir at room temperature for 16 hours. The reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography (SiO2, 20 g, Heptane/EtOAc 0-100%) to give the title compound (400 mg, 45%). MS (m/e): 526.2 (M+NH4+).

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was purified by column chromatography (SiO2, 20 g, Heptane/EtOAc 0-100%)

出典と根拠

ORDレコード
ord-edf9f4fdab1941119255d8969f0c13db
出典データセット
uspto-grants-2008_09
特許番号
US07427612B2

反応ノート

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