Ethyl formate → 9-(4-Chloro-benzenesulfonyl)-6-hydroxymethylene-7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

HRID 2354888노트

반응식

HRID 2354888 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:10]([CH2:11][C:12](=[O:27])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:28](OCC)=[O:29].[O-]CC.[Na+]>C1COCC1.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[N:16]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)(=[O:18])=[O:19])[CH:14]([CH2:13][C:12](=[O:27])[C:11]2=[CH:28][OH:29])[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 596795039-(4-Chloro-benzenesulfonyl)-7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

생성물 1

HCID 668422599-(4-Chloro-benzenesulfonyl)-6-hydroxymethylene-7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester수율 100.5%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

9-(4-Chloro-benzenesulfonyl)-7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (5.08 g, 12.2 mmol) was dissolved in THF/ethanol (40 mL, 1/1, v/v). Ethyl formate (9.84 mL, 122.4 mmol) was added followed by sodium ethoxide (12 mL of 21% solution in ethanol). The resulting mixture was stirred at room temperature for 30 minutes then heated to 60° C. for 30 minutes after which the solution was cooled back to room temperature and quenched by the addition of saturated aqueous NH4Cl (10 mL). The resulting mixture was extracted with EtOAc (3×20 mL) and the combined organic phases were dried (Na2SO4), filtered and concentrated under vacuum to yield 5.43 g (quantitative) of 9-(4-chloro-benzenesulfonyl)-6-hydroxymethylene-7-oxo-3,9-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as a yellow oil. Retention time (min)=2.114, method [1], MS (ESI) 465.0 (M+Na).

후처리

  1. temperaturethen heated to 60° C. for 30 minutes after which the solution
  2. temperaturewas cooled back to room temperature
  3. customquenched by the addition of saturated aqueous NH4Cl (10 mL)
  4. extractionThe resulting mixture was extracted with EtOAc (3×20 mL)
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-3f0ad10aa04d4911afd813b4e0cb10a8
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754712B2

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