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Cesium carbonate → HCID 68670654, 화합물

HRID 2298043
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HRID 2298043 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[N:14]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([N:17]2[CH2:18][CH2:19][CH2:20][N:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][CH2:16]2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 144749Ethyl 5-bromo-2-chlorobenzoateHCID 634876Binap, (A+-)-HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

생성물 1

HCID 68670654HCID 68670654, 화합물수율 28.9%

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매
HCID 1140Toluene용매

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온도
100 °C

실험 절차

A mixture of 5-bromo-2-chloro-benzoic acid, ethyl ester (0.50 g), hexahydro-1H-1,4-diazepine-1-carboxylic acid, 1,1-dimethylethyl ester (0.46 g), cesium carbonate (0.86 g), palladium (II) acetate (8.5 mg) and (R)-BINAP (35 mg) in toluene (3 ml) was heated at 100° C. for 14 h in a pressure vessel flushed with nitrogen. The cooled reaction mixture was poured into water and extracted (3 times) with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution and then dried over magnesium sulfate. Evaporation under reduced pressure gave an oil which was purified by chromatography over silica gel, eluting with 20% ethyl acetate in iso-hexane to yield the subtitle compound as an oil (0.21 g).

후처리

  1. customflushed with nitrogen
  2. customThe cooled reaction mixture
  3. extractionextracted (3 times) with ethyl acetate
  4. washThe combined organic extracts were washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation under reduced pressure
  7. customgave an oil which
  8. customwas purified by chromatography over silica gel
  9. washeluting with 20% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-89db27d8275a4d948ca2286c38e91ac9
출처 데이터셋
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06492355B1

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