Hydrochloric Acid → HCID 59381663, compound

HRID 2354552Notes

Reaction equation

HRID 2354552 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:12][CH2:11][N:10]2[C:13](=[O:30])[C:14]3[C:19]4[CH2:20][CH2:21][C:22]([CH:28]=[O:29])=[C:23]([S:24][CH2:25][CH2:26][CH3:27])[C:18]=4[S:17][C:15]=3[N:16]=[C:9]2[CH2:8][CH2:7]1)=[O:5])C.[OH-].[K+].O.Cl>CO>[CH3:1][O:3][C:4]([CH:6]1[CH2:12][CH2:11][N:10]2[C:13](=[O:30])[C:14]3[C:19]4[CH2:20][CH2:21][C:22]([CH:28]=[O:29])=[C:23]([S:24][CH2:25][CH2:26][CH3:27])[C:18]=4[S:17][C:15]=3[N:16]=[C:9]2[CH2:8][CH2:7]1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 59381648HCID 59381648, compound

Product 1

HCID 59381663HCID 59381663, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Compound 22 80.37 mmol) was dissolved into MeOH (10 ml), and KOH (0.98 mmol) in MeOH (5 ml) was added. The reaction mixture was stirred for 2 hours in room temperature. The reaction mixture was poured into water, acidified with HCl and extracted with CH2Cl2. Organic layer was washed with brine and dried with Na2SO4. After filtration the solvent was evaporated. Purification by flash chromatography using CH2Cl2-EtOAc 9:1 as an eluent afforded compound 23 as a major product and compound 24 as a minor product.

Workup

  1. additionwas added
  2. extractionextracted with CH2Cl2
  3. washOrganic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas evaporated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-c80509920b2f4c11ba597173c2cdc9bc
Source dataset
uspto-grants-2010_07
Patent number
US07754709B2

Reaction notes

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