Hydrochloric Acid → HCID 57771365, compound

HRID 2070599Notes

Reaction equation

HRID 2070599 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C@@H:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH2:30][CH2:29][CH2:28][C@@:19]3([CH2:23][C@@H:22]([O:24]C(=O)C)[CH2:21][CH2:20]3)[CH:18]=2)=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8].CO.[OH-].[Na+].Cl>O1CCCC1>[OH:24][C@H:22]1[CH2:21][CH2:20][C@:19]2([CH2:28][CH2:29][CH2:30][C:17]([CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([C@@H:5]([C:6]#[C:7][CH3:8])[CH2:4][C:3]([OH:31])=[O:2])=[CH:14][CH:13]=3)=[CH:18]2)[CH2:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 57771625HCID 57771625, compound

Product 1

HCID 57771365HCID 57771365, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S)-3-[4-((2S,5R)-2-acetoxy-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (107 mg) obtained in Step 1 in a mixed solvent of methanol (0.65 mL)-tetrahydrofuran (0.65 mL) was added 2N aqueous sodium hydroxide solution (0.28 mL) under ice-cooling, followed by stirring the mixture at room temperature overnight. To the reaction mixture was added 2N aqueous hydrochloric acid solution (0.28 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by thin-layer column chromatography on silica gel (acetic acid: methanol:chloroform (volume ratio)=0.1:1:20) to give (3S)-3-[4-((2S,5R)-2-hydroxy-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid (79 mg). Configuration of the structure was determined by NMR spectrum (NOESY, HSQC).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by thin-layer column chromatography on silica gel (acetic acid: methanol:chloroform (volume ratio)=0.1:1:20)

Sources & evidence

ORD record
ord-1095dc6adf2e4103a97aadd8c3b81f81
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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