m-Chloroperbenzoic acid → HCID 59717846, compound

HRID 2224687Notes

Reaction equation

HRID 2224687 reaction equation
ClC1C=CC=[C:4]([C:8]([O:10]O)=[O:9])C=1.[CH2:12]([O:14][C:15](=[O:35])[NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29](C(=O)C)=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)[CH3:13]>C(Cl)(Cl)Cl>[CH2:12]([O:14][C:15]([NH:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:27]=[CH:28][C:29]([O:10][C:8](=[O:9])[CH3:4])=[CH:30][CH:31]=2)=[CH:23][CH:24]=1)=[O:35])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59717853HCID 59717853, compound

Product 1

HCID 59717846HCID 59717846, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Metachloroperbenzoic Acid (1.2 g, 4.1 mmol) was added to a solution of {2-[4-(4-acetyl-phenoxy)-phenyl]-ethyl}-carbamic acid ethyl ester (1.0 g, 3.1 mmol) in chloroform (75 mL). Stirred at room temperature for 72 hours, quenched with saturated aqueous Na2S2O3, then extracted with dichloromethane (3×75 mL). The combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield the crude product (2 g). The crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes to yield Acetic acid 4-[4-(2-ethoxycarbonylamino-ethyl)-phenoxy]-phenyl ester (430 mg). 1H NMR (CDCl3, 300.00 MHz): 7.19-6.92 (m, 8H), 4.98 (s, 1H), 4.17-4.07 (m, 2H), 3.42 (q, 2H, J=6.6 Hz), 2.79 (t, 2H, J=7.2 Hz), 2.29 (s, 3H), 1.30-1.20 (m, 3H), 1.30-1.20 (m, 3H), 1.30-1.20 (m, 3H).

Workup

  1. customquenched with saturated aqueous Na2S2O3
  2. extractionextracted with dichloromethane (3×75 mL)
  3. dry with materialThe combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customto yield the crude product (2 g)
  7. customThe crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-a0b2b6083db44d939354ff55b064681c
Source dataset
uspto-grants-2008_05
Patent number
US07378448B2

Reaction notes

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