HCID 18973706, compound → HCID 15295207, compound

HRID 2399434Notes

Reaction equation

HRID 2399434 reaction equation
[NH2:1][C:2]([C:4]1[CH2:9][C:8]([C:23]#[N:24])([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH:20]3[CH2:22][CH2:21]3)[CH:11]=2)[CH2:7][CH2:6][C:5]=1[O:25]COC)=[O:3]>C(O)(=O)C>[NH2:1][C:2]([CH:4]1[CH2:9][C:8]([C:23]#[N:24])([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH:20]3[CH2:21][CH2:22]3)[CH:11]=2)[CH2:7][CH2:6][C:5]1=[O:25])=[O:3]

Participants

3

Reactant 1

HCID 18973706HCID 18973706, compound

Product 1

HCID 15295207HCID 15295207, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

A solution of 2-aminocarbonyl-4-cyano-4-(3-cyclopropylmethoxy-4-methoxyphenyl)-1-(methoxymethyloxy)cyclohex-1-ene (0.22 g, 0.57 mmol) in 50% aqueous acetic acid (12 mL, containing 9 drops concentrated sulfuric acid per 30 mL) was heated at 75° C. under an argon atmosphere for 2 h. The mixture was cooled, was partitioned between methylene chloride and water, was extracted twice, the organic layer was dried (potassium carbonate)and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 5% methanol/chloroform, followed by crystallization from ether/methylene chloride, provided a white powder (0.07 g, 51%): m.p. 154°-155° C.

Workup

  1. temperatureThe mixture was cooled
  2. customwas partitioned between methylene chloride and water
  3. extractionwas extracted twice
  4. customwas removed in vacuo
  5. customPurification by flash chromatography
  6. washeluting with 5% methanol/chloroform
  7. customfollowed by crystallization from ether/methylene chloride

Sources & evidence

ORD record
ord-5827e0fdfa4e4a25a47fa6c3fe47445f
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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