Water → HCID 67040947, compound

HRID 605245Notes

Reaction equation

HRID 605245 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:35]([O:37][CH2:38][C:39]([Cl:42])([Cl:41])[Cl:40])=[O:36].O>ClCCl>[Cl:40][C:39]([Cl:42])([Cl:41])[CH2:38][O:37][C:35](=[O:36])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 67040679HCID 67040679, compound

Product 1

HCID 67040947HCID 67040947, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 238c (0.85 g, 2.2 mmol) in dichloromethane (40 mL) was added pyridine (0.35 g, 4.4 mmol) and 2,2,2-trichloroethyl chloroformate (0.58 g, 2.7 mmol). The mixture was stirred at room temperature for 16 h. The reaction was poured into water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phases were washed with water, 5% HCl, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound. The residue was purified by silica gel chromatography eluting with chloroform/methanol (90:10) to give the desired product (0.90 g, 75%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  2. washThe combined organic phases were washed with water, 5% HCl, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a468ccf59eb147e28013f97a2ad2257c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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