Ethyl formate → HCID 66842302, compound

HRID 2354880Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

9-(4-Chloro-benzenesulfonyl)-7-oxo-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid ethyl ester (2.49 g, 6.45 mmol) was dissolved in THF/ethanol (14 mL, 1/1, v/v). Ethyl formate (5.19 mL, 64.53 mmol) was added followed by sodium ethoxide (6.2 mL of 21% solution in ethanol). The resulting mixture was heated to 60° C. for 30 minutes after which the solution was cooled to room temperature and quenched by the addition of saturated aqueous NH4Cl (10 mL). The resulting mixture was extracted with EtOAc (2×20 mL) and the combined organic phases were dried (Na2SO4), filtered and concentrated under vacuum to yield 2.51 g (94%) of 9-(4-chloro-benzenesulfonyl)-6-hydroxymethylene-7-oxo-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid ethyl ester as a yellow oil. Retention time (min)=2.017, method [1], MS (ESI) 414.0 (M+H).

Workup

temperaturewas cooled to room temperature
customquenched by the addition of saturated aqueous NH4Cl (10 mL)
extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
dry with materialthe combined organic phases were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-05b195cddeb24501bac9fe77758fc1c1
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754712B2

Reaction notes

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