Triethylamine → HCID 20289294, compound

HRID 1413967Notes

Reaction equation

HRID 1413967 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([OH:16])=[O:15].C(N(CC)CC)C.[CH2:27]([C:34]1[CH:38]=[CH:37][NH:36][C:35]=1[CH2:39]O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCOCC>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([O:16][CH2:39][C:35]1[NH:36][CH:37]=[CH:38][C:34]=1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 202839832-(2-Fluoro-4-trifluoromethylphenylamino)-3-methylbutanoic acidHCID 543430813-Benzyl-1-pyrrolylmethanol

Product 1

HCID 20289294HCID 20289294, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the acid chloride of 2-(2-fluoro-4-trifluoromethylphenylamino)-3-methylbutanoic acid (2.5 mmol) in ether is added 1.3 ml of triethylamine followed by 3-benzylpyrrolylmethyl alcohol (2.0 mmol) in ether over about 2 minutes. The reaction mixture is stirred for about 18 hours and then quenched with saturated aqueous sodium bicarbonate. The organic phase is washed with aqueous sodium bicarbonate, water and brine, dried over calcium sulfate and solvent evaporated. The crude product is chromatographed on a circular chromatograph eluting with 20% ether/hexane to give 3-benzylpyrrolylmethyl 2-(2-fluoro-4-trifluoromethylphenylamino)-3-methylbutanoate.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. washThe organic phase is washed with aqueous sodium bicarbonate, water and brine
  3. dry with materialdried over calcium sulfate and solvent
  4. customevaporated
  5. customThe crude product is chromatographed on a circular chromatograph
  6. washeluting with 20% ether/hexane

Sources & evidence

ORD record
ord-a0bf1b26e1e94a5aa7574cb7e7e2e8a3
Source dataset
uspto-grants-1981_02
Patent number
US04252724

Reaction notes

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