Hydrochloric Acid → HCID 86753767, compound

HRID 1417540Notes

Reaction equation

HRID 1417540 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:25][CH2:24][C@:7]2([O:11][CH2:10][C:9]([C:12]3[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][C:13]=3[O:20][CH:21]([CH3:23])[CH3:22])=[CH:8]2)[C@@H:6]1[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)=[O:4].CO.[OH-].[Na+].Cl>C1COCC1>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C@@H:6]2[C@@H:5]([C:3]([OH:4])=[O:2])[CH2:25][CH2:24][C@@:7]32[O:11][CH2:10][C:9]([C:12]2[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][C:13]=2[O:20][CH:21]([CH3:23])[CH3:22])=[CH:8]3)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86753768HCID 86753768, compound

Product 1

HCID 86753767HCID 86753767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5R,6S,7S)-6-(4-Fluorophenyl)-3-(5-cyano-2-isopropoxyphenyl)-1-oxaspiro[4.4]non-3-ene-7-carboxylic acid methyl ester(128 mg, 0.294 mmol) was taken up in THF(2 mL) and methanol (2 mL) and treated with 2.5N NaOH (0.4 mL, 1.0 mmol) for 6 hours at room temperature. 2N Hydrochloric acid (5 mL) was then added, and the product extracted with ethyl acetate (2×30 mL). The combined extracts were washed with saturated brine solution, dried (MgSO4), and evaporated to afford the title compound; yield 124 mg.

Workup

  1. extractionthe product extracted with ethyl acetate (2×30 mL)
  2. washThe combined extracts were washed with saturated brine solution
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-cb8875482d1f476d8718688c8f509a5d
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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