Methylparaben → HCID 68513427, compound

HRID 1877285Notes

Reaction equation

HRID 1877285 reaction equation
[CH:1]1([CH:7]([C:9]2[C:13]([CH3:14])=[CH:12][N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[CH:10]=2)[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=1.C(P(CCCC)CCCC)CCC.N(C([O-])=O)=NC([O-])=O>O1CCCC1>[CH:1]1([CH:7]([C:9]2[C:13]([CH3:14])=[CH:12][N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:16]=3)[CH:10]=2)[O:8][C:26]2[CH:35]=[CH:34][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 13831TributylphosphineHCID 51573101N-carboxylatoiminocarbamateHCID 68507978HCID 68507978, compound

Product 1

HCID 68513427HCID 68513427, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (15 mL) of cyclohexyl{4-methyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}methanol (0.81 g) synthesized in Example 298 (6) in tetrahydrofuran were added methyl 4-hydroxybenzoate (0.4 g), tributylphosphine (1.2 mL) and dipiperidide azodicarboxylate (1.2 g) with stirring under ice-cooling. The ice bath was removed, and the reaction mixture was stirred at room temperature overnight. Hexane was added to the reaction mixture, and the precipitate was filtered through celite. Water was added to the filtrate and the mixture was extracted with ethyl acetate. The extract was purified by silica gel chromatography (ethyl acetate:hexane=1:1, volume ratio) to give a methyl ester form of the title compound (0.96 g). This was dissolved in ethanol (5 mL), 1N sodium hydroxide (4 mL) was added at 60° C. and the mixture was stirred for 1 hr. Ethanol was evaporated under reduced pressure, and 1N hydrochloric acid (4 mL) was added to the residue to give the title compound (0.88 g, 80%) as an amorphous form.

Workup

  1. temperaturecooling
  2. customThe ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature overnight
  4. additionHexane was added to the reaction mixture
  5. filtrationthe precipitate was filtered through celite
  6. additionWater was added to the filtrate
  7. extractionthe mixture was extracted with ethyl acetate
  8. customThe extract was purified by silica gel chromatography (ethyl acetate:hexane=1:1, volume ratio)

Sources & evidence

ORD record
ord-e2b3b5f979b6469b9c252b84f5b90546
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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