Pyridine → HCID 70272188, compound

HRID 1870731Notes

Reaction equation

HRID 1870731 reaction equation
[CH2:1]([O:4][C:5](=[O:31])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]=2[NH2:30])=[CH:10][CH:9]=1)[CH:2]=[CH2:3].N1C=CC=CC=1.[C:38]1([CH2:51][O:52][C:53](Cl)=[O:54])[C:50]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]=2[CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[CH2:1]([O:4][C:5](=[O:31])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]=2[NH:30][C:53]([O:52][CH2:51][C:38]2[C:50]3[CH2:49][C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:42]=3[CH:41]=[CH:40][CH:39]=2)=[O:54])=[CH:12][CH:13]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 14261773Fluorenylmethyl chloroformateHCID 57114964HCID 57114964, compound

Product 1

HCID 70272188HCID 70272188, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

4-(2-Amino-3-benzoylphenoxymethyl)-phenoxyacetic acid allyl ester (9.03 g, 20.8 mmol) and freshly distilled pyridine (1.97 g, 25.0 mmol, 1.2 equiv) were dissolved in 100 mL of CH2Cl2. The resulting yellow solution was cooled to 0° C., and fluorenylmethoxycarbonyl chloride (4.83 g, 21.8 mmol, 1.05 equiv) was added. The resulting solution was stirred at 0° C. for 15 min and then at ambient temperature for 1 h. The solution was diluted with CH2Cl2 (150 mL), extracted twice with 1 N aqueous sodium bisulfate (100 mL), once with dilute aqueous sodium chloride (100 mL), and then concentrated to give a yellow foam. Silica gel chromatography with CH2Cl2 afforded 8.68 g (65% yield) of purified material as a white solid that was homogeneous by 1H NMR. The carboxylic acid (3-[3-Benzoyl-2-fluorenylmethoxycarbonylaminobenzoyloxymethyl]-phenoxyacetic acid) was full characterized after removal of the allyl ester.

Workup

  1. waitat ambient temperature for 1 h
  2. extractionextracted twice with 1 N aqueous sodium bisulfate (100 mL), once with dilute aqueous sodium chloride (100 mL)
  3. concentrationconcentrated
  4. customto give a yellow foam

Sources & evidence

ORD record
ord-f3fb0713cf154686aa1e9774c4ff8b6c
Source dataset
uspto-grants-2000_08
Patent number
US06100254

Reaction notes

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