m-Chloroperbenzoic acid → HCID 57999688, compound

HRID 600320Notes

Reaction equation

HRID 600320 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([C@@H:14]([NH:32][C:33]([C@@H:35]1[CH2:40][CH2:39][CH2:38][CH2:37][N:36]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:34])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([S:30][CH3:31])[CH:23]=2)=[CH:18][CH:17]=1)#[N:13]>C(Cl)Cl>[C:12]([C@@H:14]([NH:32][C:33]([C@@H:35]1[CH2:40][CH2:39][CH2:38][CH2:37][N:36]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:34])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([S:30]([CH3:31])=[O:6])[CH:23]=2)=[CH:18][CH:17]=1)#[N:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57999636HCID 57999636, compound

Product 1

HCID 57999688HCID 57999688, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (0.137 g) was added to a solution of (S)-tert-butyl 2-((S)-1-cyano-2-(4′-cyano-3′-(methylthio)biphenyl-4-yl)ethylcarbamoyl)piperidine-1-carboxylate (0.140 g) in DCM (20 mL) at 0° C. and the mixture was stirred for 2 h then allowed to warm to RT. The mixture was washed with saturated sodium bicarbonate solution, sodium metabisulfite solution, water and brine then dried over sodium sulfate and evaporated. Purification by flash silica chromatography eluting with 30-50% ethyl acetate in isohexane afforded a colourless solid (0.08 g).

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate solution, sodium metabisulfite solution, water and brine
  2. dry with materialthen dried over sodium sulfate
  3. customevaporated
  4. customPurification by flash silica chromatography
  5. washeluting with 30-50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-c309becf37b64bd695468d651f3b2688
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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