Water → HCID 86719135, compound

HRID 1844720Notes

Reaction equation

HRID 1844720 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[C:14]2[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:17]=[C:16]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[S:29]([OH:32])(=[O:31])=[O:30].CC(=O)OCC.O>C1COCC1>[CH:1]1([CH2:7][N:8]2[C:9]([C:14]3[CH:19]=[C:18]([C:20]([CH3:21])([CH3:23])[CH3:22])[CH:17]=[C:16]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:15]=3)=[CH:10][C:11]([S:29]([OH:32])(=[O:31])=[O:30])=[C:12]2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24638Chlorosulfonic acidHCID 86719133HCID 86719133, compound

Product 1

HCID 86719135HCID 86719135, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of compound 5b (1.0 g, 2.7 mmol) in THF (10 mL) was added dropwise ClSO3H (3 mL) at −78° C. This mixture was stirred at −78° C. for 3 h, then EA and cooled water was added and extracted with EA. The organic layer was washed with aq. NaHCO3, dried and concentrated to afford compound 5c (1.0 g, 83%) as yellow oil.

Workup

  1. additionwas added
  2. extractionextracted with EA
  3. washThe organic layer was washed with aq. NaHCO3
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9751e69820f04fa2b9edbebd61f0f6b1
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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