Butylamine → HCID 86754331, compound

HRID 583435Notes

Reaction equation

HRID 583435 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:6]([N:8]([CH:10]([CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:11]=[CH:12][C:13](O)=[O:14])[CH3:9])=[O:7].C(N(CC)CC)C.[CH2:45]([NH2:49])[CH2:46][CH2:47][CH3:48].C(P(=O)(OCC)OCC)#N>CN(C)C=O>[CH2:45]([NH:49][C:13](=[O:14])[CH:12]=[CH:11][CH:10]([N:8]([C:6](=[O:7])[C:5]1[CH:29]=[C:30]([C:32]([F:34])([F:35])[F:33])[CH:31]=[C:3]([C:2]([F:1])([F:37])[F:36])[CH:4]=1)[CH3:9])[CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:46][CH2:47][CH3:48]

Participants

6

Reactant 4

HCID 8007ButylamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 57046261HCID 57046261, compound

Product 1

HCID 86754331HCID 86754331, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg (0.19 mmol) of 4-[N-(3,5-bistrifluoromethyl-benzoyl)-N-methyl-amino]-5,5-diphenyl-pent-2-enoic acid and 37 μl (0.27 mmol) of triethylamine in 3 ml of N,N-dimethylformamide at 0° C. is treated with 23 μl (0.23 mmol) of butylamine, followed by 38 μl (0.23 mmol) of diethyl cyanophosphonate. After stirring for 4 h at room temperature, the reaction mixture is concentrated, diluted with ethyl acetate, and then washed with saturated sodium bicarbonate solution. The aqueous layer is further extracted with ethyl acetate (3×). The organic layers are combined, dried with sodium sulfate and concentrated. The residue is then purified by flash chromatography (95:5 methylene chloride/methanol) to give the title compound as a white solid. TLC: methylene chloride/methanol (95:5) Rf =0.23.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate solution
  4. extractionThe aqueous layer is further extracted with ethyl acetate (3×)
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is then purified by flash chromatography (95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-518e569eab6f47f4b6432be808e49070
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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