Hydrochloric Acid → 3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

HRID 643835Notes

Reaction equation

HRID 643835 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:11]([C:12](=[O:26])N[C@]2(C(OC(C)(C)C)=O)C[C@H]2C=C)[CH2:10][CH:9]([O:27]C2C3C(=CC(OC)=CC=3)N=C(C3C=CC=CC=3)C=2)[CH:8]=1)=[O:6].Cl>CO>[O:26]=[C:12]1[CH:11]2[CH2:10][CH:9]([CH2:8][CH:7]2[C:5]([OH:4])=[O:6])[O:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 592041875-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acid methyl ester

Product 1

HCID 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (1M, 74 mL, 0.074 mol) was added to a stirred solution of 30 (3.73 g, 0.018 mol) in methanol (105 mL) at room temperature. After 4 h, the reaction mixture was neutralized with 3M HCl, evaporated and co-evaporated with toluene several times. Pyridine (75 mL) and Ac2O (53 mL) were added and the reaction mixture was allowed to shake overnight at room temperature. The mixture was then co-evaporated with toluene and purified by flash column chromatography (ethyl acetate+1% acetic acid) to give the title compound (2.51 g, 88%) as a yellow oil.

Workup

  1. customevaporated
  2. additionPyridine (75 mL) and Ac2O (53 mL) were added
  3. waitto shake overnight at room temperature
  4. custompurified by flash column chromatography (ethyl acetate+1% acetic acid)

Sources & evidence

ORD record
ord-857a6a3b613749dab517a62fd97aa7e8
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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