Hydrochloric Acid → HCID 118510801, compound

HRID 1053801Notes

Reaction equation

HRID 1053801 reaction equation
[Li+].[OH-].[OH:3][CH:4]([CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1)/[CH:5]=[CH:6]/[C@H:7]1[CH2:11][CH2:10][C:9](=[O:12])[C@@H:8]1[CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=1.Cl>C1COCC1>[OH:3][CH:4]([CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1)/[CH:5]=[CH:6]/[C@H:7]1[CH2:11][CH2:10][C:9](=[O:12])[C@@H:8]1[CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118510796HCID 118510796, compound

Product 1

HCID 118510801HCID 118510801, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

LiOH (240 mL, 0.24 mmol, 1 M) was added to a solution of methyl 4-(2-((1R,2R)-2-((E)-3-hydroxy-4-(naphthalen-2-yl)but-1-en-1-yl)-5-oxocyclopentyl)ethyl)benzoate (21 mg, 0.047 mmol) in THF (2.5 mL). The mixture was stirred at 60° C. overnight, cooled to room temperature and then 1 M HCl (20 mL) was added. The resulting mixture was extracted with CH2Cl2 (3×20 mL) and the combined organic solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification by preparative thin layer chromatography (10% methanol/CH2Cl2) gave the title compound (13 mg).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe resulting mixture was extracted with CH2Cl2 (3×20 mL)
  3. washthe combined organic solution was washed with brine
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by preparative thin layer chromatography (10% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-9aa4207809ba49989f0e03cde3e918bb
Source dataset
uspto-grants-2016_07
Patent number
US09394273B2

Reaction notes

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