Hydrochloric Acid → HCID 54141701, compound

HRID 1263276Notes

Reaction equation

HRID 1263276 reaction equation
C([O:4][CH:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:6]=[CH:7][CH:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[CH2:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO.[Cl-].[Na+]>[OH:4][CH:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:6]=[CH:7][CH:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[CH2:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 54499152HCID 54499152, compound

Product 1

HCID 54141701HCID 54141701, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

To a solution of 13 (100 mg, 0.25 mmol) in methanol (3 mL) was added potassium carbonate (220 mg, 1.59 mmol). The reaction mixture was stirred at room temperature for five hours before it was acidified with 10% hydrochloric acid to pH 2. It was then diluted with saturated aqueous sodium chloride and extracted with ether three times. The combined ether layer was washed with saturated sodium chloride and dried over magnesium sulfate. Removal of the solvent afforded 70 mg of 7-[2-(3-hydroxy-1-octen-1-yl)-5-oxopyrrolidin-1-yl]-6-oxo-1-heptanoic acid (14). IR (CH2Cl2): 3600-2500 (br), 1720, 1690 cm-1 ; PMR (CDCl3): δ5.67 (bs, 2H, --CO2H and --OH), 5.67-5.17 (m, 2H), 4.33-3.56 (m, 4H), 2.57-2.13 (m, 6H), 1.90-1.07 (m, 14H), and 0.90 (t, 3H); MS: m/z 335 (M+ --H2O).

Workup

  1. extractionextracted with ether three times
  2. washThe combined ether layer was washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-7372fab7684e4981a172031ad2686913
Source dataset
uspto-grants-1984_06
Patent number
US04456613

Reaction notes

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