Cesium carbonate → tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-(2-(cyclopropylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

HRID 1051021ノート

反応式

HRID 1051021 の反応式
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:39][C:40]([NH:42][CH:43]1[CH2:45][CH2:44]1)=[O:41]>CN(C)C=O>[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:39][C:40]([NH:42][CH:43]4[CH2:45][CH2:44]4)=[O:41])[CH:16]=3)(=[O:13])=[O:14])[CH:10]=[C:9]([CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 167575602-Bromo-N-cyclopropylacetamideHCID 90168594tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

生成物 1

HCID 90168922tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-(2-(cyclopropylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

tert-Butyl ((5-(cyclo ex-1-en-1-yl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 7d (100 mg, 0.22 mmol) was dissolved in 20 mL of N,N-dimethylformamide, followed by addition of cesium carbonate (146 mg, 0.45 mmol) and 2-bromo-N-cyclopropyl-acetamide (79 mg, 0.45 mmol, prepared by a known method disclosed in “Journal of Medicinal Chemistry, 1987, 30(1), 20-24”), and then the reaction solution was stirred for 16 h. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by thin layer chromatography with elution system C to obtain the title product tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-(2-(cyclopropylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 7e (117 mg, a light yellow oily product) in 98% yield.

後処理

  1. customprepared by a known method
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe resulting residue was purified by thin layer chromatography with elution system C

出典と根拠

ORDレコード
ord-fb9c7ea55fbe447ea2a203f707e4eb76
出典データセット
uspto-grants-2016_07
特許番号
US09388133B2

反応ノート

読み込み中…