m-Chloroperbenzoic acid → Acetic acid 1-ethylcarbamoyl-7-oxiranylmethyl-1H-indazol-6-yl ester

HRID 1815940Notes

Reaction equation

HRID 1815940 reaction equation
[CH2:1]([C:4]1[C:5]([O:18][C:19](=[O:21])[CH3:20])=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([C:13](=[O:17])[NH:14][CH2:15][CH3:16])[N:10]=[CH:9]2)[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[CH2:15]([NH:14][C:13]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([O:18][C:19](=[O:21])[CH3:20])[C:4]=2[CH2:1][CH:2]2[CH2:3][O:30]2)[CH:9]=[N:10]1)=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69564705Acetic Acid 7-allyl-1-ethylcarbamoyl-1H-indazol-6-yl ester

Product 1

HCID 86759647Acetic acid 1-ethylcarbamoyl-7-oxiranylmethyl-1H-indazol-6-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step D (2.70 g, 9.4 mmol) in dichloromethane (15 mL) was added 3-chloro-perbenzoic acid (2.31 g, 10.3 mmol, 77% pure) and the mixture stirred at ambient temperature for 1 h. Additional 3-chloro-perbenzoic (0.2 g, 0.9 mmol) was added and the reaction continued for 3 h. The reaction was quenched with saturated aqueous sodium bicarbonate (100 mL) and extracted with dichloromethane (50 mL). The extract was dried (MgSO4) and evaporated to a white solid (1.59 g, 56%): mp 110-111° C.; LC/MS (+APCI) m/z 304 (M+H).

Workup

  1. additionAdditional 3-chloro-perbenzoic (0.2 g, 0.9 mmol) was added
  2. waitthe reaction continued for 3 h
  3. customThe reaction was quenched with saturated aqueous sodium bicarbonate (100 mL)
  4. extractionextracted with dichloromethane (50 mL)
  5. dry with materialThe extract was dried (MgSO4)
  6. customevaporated to a white solid (1.59 g, 56%)

Sources & evidence

ORD record
ord-98f4503d5c8247e6ac872ab2cd117c55
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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