m-Chloroperbenzoic acid → HCID 22258888, compound

HRID 1611219Notes

Reaction equation

HRID 1611219 reaction equation
[NH2:1][C:2]1[N:14]=[C:13]([C:15]2[C:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[CH:19][CH:18]=[CH:17][C:16]=2[O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH:12]=[C:11]([S:36][CH3:37])[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C1C=C(Cl)C=C(C(OO)=[O:46])C=1>C(Cl)Cl>[NH2:1][C:2]1[N:14]=[C:13]([C:15]2[C:20]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=3)=[CH:19][CH:18]=[CH:17][C:16]=2[O:31][CH2:32][CH:33]2[CH2:34][CH2:35]2)[CH:12]=[C:11]([S:36]([CH3:37])=[O:46])[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22258882HCID 22258882, compound

Product 1

HCID 22258888HCID 22258888, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of tert-butyl 2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-4-(methylsulfanyl)nicotinate (1.72 g, 3.30 mmol) in CH2Cl2 (20 mL) was added m-CPBA (69%, 0.82 g, 3.30 mmol). The reaction mixture was stirred at 0° C. for 15 min, quenched with saturated aqueous NaHCO3 solution (20 mL) containing Na2S2O3 (1 g). The organic phase was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by column chromatography on silica gel (hexane/ethyl acetate=3:2 to 1:1) gave solid, which was triturated with ethyl acetate and diisoproyl ether to give tert-butyl 2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-4-(methylsulfinyl)nicotinate as a white powder (1.112 g, yield; 63%).

Workup

  1. customquenched with saturated aqueous NaHCO3 solution (20 mL)
  2. additioncontaining Na2S2O3 (1 g)
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography on silica gel (hexane/ethyl acetate=3:2 to 1:1)
  8. customgave solid, which
  9. customwas triturated with ethyl acetate and diisoproyl ether

Sources & evidence

ORD record
ord-3221bd41b461440eaedfdd6f8de8817b
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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