m-Chloroperbenzoic acid → HCID 86755677, compound

HRID 651164Notes

Reaction equation

HRID 651164 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C@H:19]([NH:28][C:29]([C:31]1[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([Cl:40])=[CH:35][CH:34]=2)=[O:30])[C:20](=[O:27])[N:21]1[CH2:26][CH2:25][S:24][CH2:23][CH2:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.C(OCC)(=O)C>[CH2:12]([C@H:19]([NH:28][C:29]([C:31]1[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([Cl:40])=[CH:35][CH:34]=2)=[O:30])[C:20](=[O:27])[N:21]1[CH2:22][CH2:23][S:24](=[O:6])[CH2:25][CH2:26]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57143767HCID 57143767, compound

Product 1

HCID 86755677HCID 86755677, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

m-Chloroperoxybenzoic acid (80 mg of 50%, 0.23 mmol) was added at 25° C. to a solution of 5chloro-1H-indole-2-carboxylic acid ((1S)-benzyl-2-oxo-2-thiomorpholin-4-yl-ethyl)-amide (100 mg, 0.23 mmol) in dichloromethane (2 mL). After 1 hour, the mixture diluted with ethyl acetate and washed three times with a 50/50 mixture of saturated aqueous sodium bicarbonate and 10% aqueous sodium thiosulfate, once with saturated aqueous sodium bicarbonate, brine, and dried. The crude product was purified by column chromatography on silica gel eluted with 0.5-8% ethanol in dichloromethane to give the title compound. Yield 76%; HPLC (60/40) 3.97 minutes (97%); mp 230-234° C.; TSPMS 444/446 (MH+, 100%);

Workup

  1. washwashed three times
  2. additionwith a 50/50 mixture of saturated aqueous sodium bicarbonate and 10% aqueous sodium thiosulfate
  3. dry with materialonce with saturated aqueous sodium bicarbonate, brine, and dried
  4. customThe crude product was purified by column chromatography on silica gel
  5. washeluted with 0.5-8% ethanol in dichloromethane

Sources & evidence

ORD record
ord-ca17788174cd42f5b85f0778a11a204f
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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