Triethylamine → HCID 58899080, compound

HRID 2246053Notes

Reaction equation

HRID 2246053 reaction equation
[NH2:1][CH:2]([CH:7]([N:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:15]=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[C:27]([C:34]([F:37])([F:36])[F:35])[CH:26]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(Cl)Cl.C1COCC1>[CH2:17]([N:14]([CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]([NH:1][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][C:25]([F:24])=[CH:26][C:27]=1[C:34]([F:37])([F:35])[F:36])[C:3]([O:5][CH3:6])=[O:4])[CH:15]=[O:16])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 6882554-Fluoro-2-(trifluoromethyl)benzoic acidHCID 59217673HCID 59217673, compound

Product 1

HCID 58899080HCID 58899080, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.4 g (0.0052 mol) of methyl 2-amino-3-(N-benzyl-N-formylamino)-3-phenylpropionate were dissolved in methylene chloride, and 1.0 g (0.0052 mol) of 4-fluoro-2-trifluoromethylbenzoic acid and 1.0 g (0.010 mol) of triethylamine in THF were added. At 0-5° C., 1.3 g (0.0052 mol) of bis(2-oxo-3-oxazolidinyl)phosphoryl chloride were added. After 2 h at 0° C., the mixture was stirred at room temperature for 15 h. The solvents were removed and the residue was taken up in ethyl acetate, washed and dried. Chromatographic purification (silica gel column, cyclohexane/ethyl acetate) gave 0.65 g of the title compound as a colorless oil.

Workup

  1. customThe solvents were removed
  2. washwashed
  3. customdried
  4. customChromatographic purification (silica gel column, cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-074db0345c0a436d84310fee32c5df57
Source dataset
uspto-grants-2010_03
Patent number
US07687435B2

Reaction notes

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