m-Chloroperbenzoic acid → HCID 86694360, compound

HRID 538930Notes

Reaction equation

HRID 538930 reaction equation
[CH:1]1([N:6]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])(=[O:16])=[O:15])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][CH2:4][CH:3]=[CH:2]1.C([O-])(O)=[O:27].[Na+].ClC1C=C(C=CC=1)C(OO)=O>C(Cl)Cl>[C@H:2]12[O:27][C@H:3]1[CH2:4][CH2:5][C@@H:1]2[N:6]([S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24])(=[O:16])=[O:15])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86694361HCID 86694361, compound

Product 1

HCID 86694360HCID 86694360, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of tert-butyl cyclopent-2-en-1-yl((2-nitrophenyl)sulfonyl)carbamate (2.75 g, 7.46 mmol) and NaHCO3 (1.254 g, 14.93 mmol) in CH2Cl2 (60 mL) was added in one portion meta-chloroperoxybenzoic acid (2.58 g, 14.93 mmol). The resulting reaction mixture was stirred overnight at RT. The reaction mixture was diluted with CH2Cl2 and washed with 20% aqueous Na2SO3 solution, saturated NaHCO3 solution and water. The organic phase was dried over MgSO4 and concenrated. The title compound was obtained after crystallization from EtOAc as white crystals (2.01 g, 68%): TLC (heptane-EtOAc 1:1) Rf=0.48; tR=1.20 min (UPLC 1), tR=1.12 min (LC-MS 3); ESI-MS: 329 [M-isobutylene]+ (LC-MS 3).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 20% aqueous Na2SO3 solution, saturated NaHCO3 solution and water
  3. dry with materialThe organic phase was dried over MgSO4

Sources & evidence

ORD record
ord-8608caf4816f44b8816728f5385207e2
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

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