Hydrochloric Acid → HCID 25255736, compound

HRID 2070541Notes

Reaction equation

HRID 2070541 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C@@H:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH2:18][C:19]3([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:20][CH2:21][CH:22]=2)=[CH:11][CH:10]=1)[C:6]#[C:7][CH3:8].O1CCCC1.[OH-].[Na+].Cl>CO>[CH2:18]1[C:19]2([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:20][CH2:21][CH:22]=[C:17]1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C@@H:5]([C:6]#[C:7][CH3:8])[CH2:4][C:3]([OH:28])=[O:2])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57771576HCID 57771576, compound

Product 1

HCID 25255736HCID 25255736, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-3-[4-(spiro[5.5]undec-2-en-2-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (0.82 g) obtained in Step 8 in a mixed solvent of tetrahydrofuran (4 mL)-methanol (4 mL) was added 2N aqueous sodium hydroxide solution (2 mL), followed by stirring the reaction mixture at room temperature for 14 hours. Then, after addition of 1N aqueous hydrochloric acid solution, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:1) to give (S)-3-[4-(spiro[5.5]undec-2-en-2-ylmethoxy)-phenyl]-hex-4-ynoic acid (0.77 g) as the desired compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:1)

Sources & evidence

ORD record
ord-275ef5d8152a4fab9cb5423b39ef42fb
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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