Methane → HCID 13773297, compound

HRID 1651458Notes

Reaction equation

HRID 1651458 reaction equation
C([S:4][CH2:5][CH2:6][C:7]([N:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:11][CH:10]1[C:20]([O:22]CC)=[O:21])=[O:8])(=O)C.[OH-].[K+].C>CO.O.ClCCl>[SH:4][CH2:5][CH2:6][C:7]([N:9]1[N:13]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:11][CH:10]1[C:20]([OH:22])=[O:21])=[O:8]

Participants

7

Reactant 3

HCID 297MethaneHCID 14797Potassium HydroxideHCID 13773296HCID 13773296, compound

Product 1

HCID 13773297HCID 13773297, compoundYield 20.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product from step (c) (1.44 g) in methanol (40 ml) was cooled to 15° under nitrogen and treated dropwise with a solution of potassium hydroxide (0.69 g) in water (40 ml). The mixture was stirred at room temperature for 2 hours and then the solvents were evaporated. The residue was taken up in water and washed with ether. The aqueous phase was acidified with 2N HCl and extracted with ethyl acetate. The separated organic phase was washed with water, dried and evaporated. The residue was purified by flash chromatography to give a pale yellow solid. The solid was taken up in dichloromethane, treated with charcoal, filtered and the filtrate evaporated to give the title product (0.24 g) as an off-white solid. mp 106°-9°.

Workup

  1. customthe solvents were evaporated
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. washThe separated organic phase was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. customto give a pale yellow solid
  9. filtrationfiltered
  10. customthe filtrate evaporated

Sources & evidence

ORD record
ord-3289f5c5f48446828dda7ab7a4c5f625
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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