Carbon Tetrachloride → HCID 12043645, compound

HRID 2227732Notes

Reaction equation

HRID 2227732 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][CH2:15][CH:16]([C:18](OC)=[O:19])[N:17]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.COC(=O)[C@H](CO)[NH:28]C(=O)C1C=CC(OC2C=CC(F)=CC=2)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C.C(Cl)(Cl)(Cl)Cl>C(#N)C>[F:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][CH:15]=[C:16]([C:18]([NH2:28])=[O:19])[N:17]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 5943Carbon Tetrachloride2×HCID 11776Triphenylphosphine2×HCID 81531Diisopropylethylamine2×HCID 22718111HCID 22718111, compoundHCID 54283856HCID 54283856, compound

Product 1

HCID 12043645HCID 12043645, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4,5-dihydro-2-[4-(4-fluorophenoxy)phenyl]oxazole-4-carboxylate. To a solution of N-[4-(4-fluorophenoxy)benzoyl]-L-serine methyl ester (assumed to be 37 mmol from the previous reaction) and triphenylphosphine (0.38 g, 6.8 mmol) in acetonitrile (40 mL) was added diisopropylethyl amine (1.2 ml, 6.8 mmol) and carbon tetrachloride (0.66 mL, 6.8 mmol). The resulting solution was stirred at room temperature for 48 hours when TLC analysis indicated incomplete reaction. Triphenylphosphine (1.9 g, 7.2 mmol), diisopropylethyl amine (1.2 mL, 6.8 mmol) and carbon tetrachloride (0.66 mL, 6.8 mmol) was added to the reaction. The solution was stirred at room temperature for 16 hours and concentrated to dryness. The resulting solid was purified by column chromatography affording 910 mg (89%) of the desired product. 1H NMR (DMSO-d6): 7.88 (d, J=8.7 Hz, 2H), 7.29 (t, J=9.3 Hz, 2H), 7.20-7.17 (m, 2H), 7.03 (d, J=8.7 Hz, 2H), 4.95 (dd, J=8.1 Hz, 1H), 4.64-4.25 (m, 2H), 3.71 (s, 3H).

Workup

  1. customreaction
  2. stirringThe solution was stirred at room temperature for 16 hours
  3. concentrationconcentrated to dryness
  4. customThe resulting solid was purified by column chromatography

Sources & evidence

ORD record
ord-e2f66723ca9d4a5185731538be7b41cc
Source dataset
uspto-grants-2002_07
Patent number
US06414011B1

Reaction notes

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