Hydrochloric Acid → HCID 57771434, compound

HRID 2070590Notes

Reaction equation

HRID 2070590 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].O1CCCC1.[OH-].[Na+].Cl>CO>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57771456HCID 57771456, compound

Product 1

HCID 57771434HCID 57771434, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-3-[4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (23.5 g) obtained in Step 4 in a mixed solvent of tetrahydrofuran (94 mL)-methanol (94 mL) was added 2N aqueous sodium hydroxide solution (48 mL), followed by stirring the mixture at room temperature overnight. To the reaction mixture was added 2N aqueous hydrochloric acid solution (48 mL), followed by extraction with n-hexane twice. The organic layers were combined, washed with saturated brine, dried and concentrated to give (R)-3-[4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid (26 g).

Workup

  1. extractionfollowed by extraction with n-hexane twice
  2. washwashed with saturated brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f076989523d45c4b3a494127ba63708
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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