Ethylene Glycol → HCID 59268882, compound

HRID 2061594Notes

Reaction equation

HRID 2061594 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].[CH2:26](O)[CH2:27][OH:28]>C(Cl)Cl>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([N:14]2[CH:12]3[CH2:13][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH:8]2[CH2:9][C:10]2([CH2:11]3)[O:28][CH2:27][CH2:26][O:25]2)(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 59679493HCID 59679493, compound

Product 1

HCID 59268882HCID 59268882, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-(4-chloro-benzenesulfonyl)-7-oxo-9-aza-bicyclo[3.3.1]nonane-3-carboxylic acid ethyl ester (6) (1.62 g, 4.19 mmol) in CH2Cl2 (14 mL) was added ethylene glycol (0.94 mL, 16.7 mmol) and TMSC1 (1.06 mL, 8.39 mmol). The resulting solution was heated to reflux for 48 h and was subsequently washed with saturated aqueous NaHCO3 (10 mL). The organic phase was dried (Na2SO4), filtered and concentrated under vacuum to yield 1.62 g (90%) of compound 50. MS (ESI) 430.1 (M+H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 48 h
  3. washwas subsequently washed with saturated aqueous NaHCO3 (10 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7e173237f970431bbb46b7e4902a4b5a
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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