Hydrochloric Acid → HCID 22010166, compound

HRID 322867Notes

Reaction equation

HRID 322867 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:30])[CH:16]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[CH3:29])[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.Cl>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:30])[CH:16]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[CH3:29])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 54489194HCID 54489194, compound

Product 1

HCID 22010166HCID 22010166, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl (RS)-5-(3-benzyloxy-phenyl)-4-(3-methylpyrid-4-yl)-5-oxopentanoate (3.26 g), dioxan (50 mL), water (9 mL) and concentrated hydrochloric acid (6 mL) is stirred at 60° C. for 1 hour and then evaporated to dryness under reduced pressure. The residue is treated with saturated aqueous sodium bicarbonate solution to give a solution of pH 7 and extracted with ethyl acetate. Evaporation, followed by crystallisation from a mixture of ethyl acetate and pentane affords (RS)-5-(3-benzyloxyphenyl)-4-(3-methylpyrid-4-yl)-5-oxopentanoic acid (1.56 g) in the form of a cream coloured solid, m.p. 55-57° C. [Elemental analysis:- C,73.7;H,5.92; N,3.41%. Calculated:- C,74.0;H,5.95;N,3.60%].

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionThe residue is treated with saturated aqueous sodium bicarbonate solution
  3. customto give a solution of pH 7
  4. extractionextracted with ethyl acetate
  5. customEvaporation
  6. customfollowed by crystallisation from a mixture of ethyl acetate and pentane

Sources & evidence

ORD record
ord-4a60fc5284b64333b9a040ceb9779ea5
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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