m-Chloroperbenzoic acid → HCID 178451080, compound

HRID 1035738Notes

Reaction equation

HRID 1035738 reaction equation
[CH2:1]([S:8][CH2:9][C:10]1[S:14][C:13]([NH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([C@H:24]3[CH2:29][CH2:28][C@H:27]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[O:17])=[N:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:46])C=1>ClCCl>[C:2]1([CH2:1][S:8]([CH2:9][C:10]2[S:14][C:13]([NH:15][C:16]([C:18]3[CH:19]=[CH:20][C:21]([C@H:24]4[CH2:29][CH2:28][C@H:27]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26][CH2:25]4)=[CH:22][CH:23]=3)=[O:17])=[N:12][N:11]=2)=[O:46])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 178451079HCID 178451079, compound

Product 1

HCID 178451080HCID 178451080, compoundYield 118.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.1 g of tert-butyl trans-{4-[4-(5-benzylsulfanylmethyl[1.3.4]thiadiazol-2-ylcarbamoyl)-phenyl]cyclohexyl}acetate (0.11 mmol, 1 eq.) is placed in 10 mL of dichloromethane with stirring. 0.027 g of 70% meta-chloroperbenzoic acid (0.11 mmol, 1 eq.) is added. After 2 hours, 0.01 g of 70% meta-chloroperbenzoic acid (0.41 mmol, 0.37 eq.) is added. After 16 hours, the reaction medium is diluted with dichloromethane and washed with saturated aqueous sodium hydrogen carbonate solution. The organic phase is dried and evaporated. The residue is triturated in ethyl acetate to give 0.072 g of tert-butyl trans-{4-[4-(5-phenylmethanesulfinylmethyl[1.3.4]thiadiazol-2-ylcarbamoyl)-phenyl]cyclohexyl}acetate.

Workup

  1. waitAfter 16 hours
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. customThe organic phase is dried
  4. customevaporated
  5. customThe residue is triturated in ethyl acetate

Sources & evidence

ORD record
ord-6fe10f64826a41268c76ad771b528bc9
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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