Hydrochloric Acid → HCID 42602611, compound

HRID 2070551Notes

Reaction equation

HRID 2070551 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C@@H:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH2:26][CH2:25][CH2:24][C:19]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:18]=2)=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8].[OH-].[Na+].Cl.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.CO.O1CCCC1>[CH2:20]1[C:19]2([CH2:24][CH2:25][CH2:26][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:27])=[O:2])=[CH:14][CH:13]=3)=[CH:18]2)[CH2:23][CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 57771623HCID 57771623, compound

Product 1

HCID 42602611HCID 42602611, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-[4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (1.33 g) obtained in Step 7 in a mixed solvent of tetrahydrofuran (13 mL)-methanol (13 mL) was added 2N aqueous sodium hydroxide solution (4.6 mL), followed by stirring the reaction mixture at room temperature overnight. Then, to the reaction mixture were added successively 2N aqueous hydrochloric acid solution (5.1 mL), ethyl acetate (100 mL) and sodium sulfate (50 g), followed by stirring for 30 minutes. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=20:80) to give (S)-3-[4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid (895 mg) as the desired compound.

Workup

  1. stirringby stirring for 30 minutes
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=20:80)

Sources & evidence

ORD record
ord-a534f1763e494cae8030e3dd0d943216
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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