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Potassium Carbonate → 7-(2-{1-[2-(4-Cyanophenoxy)ethyl]ureido}ethyl)-9-oxa-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylic acid tert-butyl ester

HRID 899125
ノート
印刷プレビュー

反応式

HRID 899125 の反応式
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1)#[N:2].[C:29]([O:33][C:34]([N:36]1[CH2:43][CH:42]2[O:44][CH:38]([CH2:39][NH:40][CH2:41]2)[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].C([O-])([O-])=O.[K+].[K+].[Br-].[Li+]>C(#N)C>[C:29]([O:33][C:34]([N:36]1[CH2:37][CH:38]2[O:44][CH:42]([CH2:41][N:40]([CH2:15][CH2:14][N:10]([CH2:9][CH2:8][O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:28][CH:27]=3)[C:11]([NH2:13])=[O:12])[CH2:39]2)[CH2:43]1)=[O:35])([CH3:32])([CH3:30])[CH3:31]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 82050Lithium BromideHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 86616242Toluene-4-sulfonic acid 2-{1-[2-(4-cyanophenoxy)ethyl]ureido}ethyl ester

生成物 1

HCID 690740097-(2-{1-[2-(4-Cyanophenoxy)ethyl]ureido}ethyl)-9-oxa-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylic acid tert-butyl ester

試薬・触媒・溶媒

1
HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

A mixture of toluene-4-sulfonic acid 2-{1-[2-(4-cyanophenoxy)ethyl]-ureido}ethyl ester (15 g, 0.0372 mol, 1.0 eq.; see Preparation D above), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (8.525 g, 0.0372 mol, 1.0 eq.; see WO 01/28992), fused K2CO3 (7.7 g, 0.0558 mol, 1.5 eq.) and lithium bromide (9.6 g, 0.1116 mol, 3.0 eq.) in dry acetonitrile (350 mL) was heated to 40° C. under N2 for 4 days. The reaction was cooled to rt, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography over silica gel, using 3% methanol and DCM as eluent, to yield the sub-title compound as a white solid. Yield: 7 g, 40.9%.

後処理

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography over silica gel

出典と根拠

ORDレコード
ord-c71c1595f5084081b31806ce941006da
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07354917B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート