Triethylamine → N-(3-benzoylphenyl) 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamide

HRID 892801Notes

Reaction equation

HRID 892801 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:10]([C:19]([OH:21])=O)[CH2:9][S:8]2)[CH:2]=1.[NH2:22][C:23]1[CH:24]=[C:25]([CH:34]=[CH:35][CH:36]=1)[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(Cl)Cl>[C:26]([C:25]1[CH:24]=[C:23]([NH:22][C:19]([CH:10]2[CH2:9][S:8][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[N:11]2[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[O:21])[CH:36]=[CH:35][CH:34]=1)(=[O:27])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 17817Methanone, (3-aminophenyl)phenyl-HCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 14772789N-tert-butoxycarbonyl-2-(3-pyridyl)thiazolidine-4-carboxylic acid

Product 1

HCID 19894104N-(3-benzoylphenyl) 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamideYield 115%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxylic acid (944 mg; 1.2 eq.; 3.05 mmoL), prepared as described above, and 3-aminobenzophenone (500 mg; 2.54 mmol) in methylene chloride (0.15M) was added triethylamine (0.46 mL) at room temperature under nitrogen with stirring, followed by addition of bis(2-oxo-3-oxazolidinyl)phosphinic chloride (773 mg; 1.2 eq) and the resulting mixture was stirred at ambient temperature for 16 hours. This mixture was concentrated to an oil on a rotory evaporator which was partitioned between ethyl acetate (30 mL) and sodium bicarbonate (30 mL). The aqueous phase was extracted twice with ethyl acetate and the resulting combined organic layers were washed with brine and dried magnesium sulfate. After filtering, the solvent was removed to yield the title compound (1.43 g) as a thick orange oil. The compound was further purified by flash chromatography on silica gel to yield 1010 mg (82% yield) N-(3-benzoylphenyl) 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamide as a white foam.

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 16 hours
  2. concentrationThis mixture was concentrated to an oil on a rotory evaporator which
  3. customwas partitioned between ethyl acetate (30 mL) and sodium bicarbonate (30 mL)
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washwere washed with brine and dried magnesium sulfate
  6. filtrationAfter filtering
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-0ccfc005bc614e3d86d22a2c276c0ff9
Source dataset
uspto-grants-1992_06
Patent number
US05120751

Reaction notes

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