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 1393224ノート

反応式

HRID 1393224 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-19956cbb15e0401eb6c25a35d4c77913
出典データセット
uspto-grants-2008_03
特許番号
US07345056B2

反応ノート

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