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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
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HRID 899125 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매

1
HCID 6342Acetonitrile용매

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온도
40 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-c71c1595f5084081b31806ce941006da
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07354917B2

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