Sodium ethoxide → HCID 67177219, compound

HRID 2362220Notes

Reaction equation

HRID 2362220 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([CH:12]3[C:21](=[O:22])[CH2:20][CH2:19][C:14]4([O:18][CH2:17][CH2:16][O:15]4)[CH2:13]3)=[O:11])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[O-:23][CH2:24][CH3:25].[Na+]>C(O)C>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][CH2:19][C:14]1([CH2:13][CH2:12][C:10]([C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][S:1][C:5]=3[CH:6]=2)=[O:11])[O:18][CH2:17][CH2:16][O:15]1)[CH3:25]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 67233299HCID 67233299, compound

Product 1

HCID 67177219HCID 67177219, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, 7-(Benzothiazole-6-carbonyl)-1,4-dioxa-spiro[4.5]decan-8-one (271 mg, 0.85 mmol) was dissolved in ethanol (1 mL). 2.43 M sodium ethoxide solution (0.01 mL, 0.03 mmol) was added. After 12 hrs, reaction was concentrated in vacuo. The residue was diluted with 10 mL EtOAc/5 mL 10% citric acid. The layers were separated. The aqueous layer was further extracted with EtOAc (3×3 mL). The combined organic layers were washed with water (5 mL) and brine (5 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column (40% EtOAc/hexanes) to yield 3-[2-(3-Benzothiazol-6-yl-3-oxo-propyl)-[1,3]dioxolan-2-yl]-propionic acid ethyl ester (19C) (100 mg, 38%, light yellow oil).

Workup

  1. customreaction
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with 10 mL EtOAc/5 mL 10% citric acid
  4. customThe layers were separated
  5. extractionThe aqueous layer was further extracted with EtOAc (3×3 mL)
  6. washThe combined organic layers were washed with water (5 mL) and brine (5 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by silica gel column (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ba3cc3b430d148f9a8671f18fbb0eb93
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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