Methanol → HCID 53703941, compound

HRID 1701160Notes

Reaction equation

HRID 1701160 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.CO.[CH:24]1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1>[CH3:24][O:20][C:19](=[O:21])[CH2:18][S:16]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:9][CH:10]=1)[CH3:15])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 20348737HCID 20348737, compound

Product 1

HCID 53703941HCID 53703941, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

800 gm (2.61 mol) of the difficultly soluble diastereoisomer of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid, m.p. 164°-165° C., were suspended in 4 liters of benzene and 125.5 gm (3.92 mol) of methanol, and a solution of 648 gm (3.14 mol) of dicyclohexyl-carbodiimide in 650 ml of benzene was added while stirring and cooling at 20°-25° C. The acid dissolved, and dicyclohexylurea precipitated out. The mixture was allowed to stand overnight at room temperature, then the excess of carbodiimide was decomposed by addition of glacial acetic acid, and then 2 liters of water were added, the dicyclohexylurea was suction-filtered off, the organic phase was separated from the filtrate and evaporated in vacuo after drying. The obtained oil (969 gm) was recrystallized from 2.9 liters of isopropanol. Yield: 736 gm (88% of theory); m.p. 75°-77° C.

Workup

  1. temperaturecooling at 20°-25° C
  2. dissolutionThe acid dissolved
  3. customdicyclohexylurea precipitated out
  4. additionthe excess of carbodiimide was decomposed by addition of glacial acetic acid
  5. addition2 liters of water were added
  6. filtrationthe dicyclohexylurea was suction-filtered off
  7. customthe organic phase was separated from the filtrate
  8. customevaporated in vacuo
  9. customafter drying
  10. customThe obtained oil (969 gm) was recrystallized from 2.9 liters of isopropanol

Sources & evidence

ORD record
ord-e4be456d88074e8289827e72fede01a5
Source dataset
uspto-grants-1980_03
Patent number
US04191776

Reaction notes

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