m-Chloroperbenzoic acid → HCID 66622555, compound

HRID 416307Notes

Reaction equation

HRID 416307 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:28])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][CH2:19][C@H:18]([S:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:17]2)=[CH:12][CH:11]=1.C1C=C(Cl)C=C(C(OO)=[O:37])C=1>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:28])[C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:20][CH2:19][C@H:18]([S@@:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[O:37])[CH2:17]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11574654HCID 11574654, compound

Product 1

HCID 66622555HCID 66622555, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 378 (15 mg, 0.04 mmol) and mCPBA (6 mg, 0.04 mmol) in DCM (2 mL) was stirred at room temperature for 1 hour. The reaction mixture was concentrated and the residue was purified by flash chromatography using the gradient EtOAc to 5% MeOH in DCM as an eluent, to afford the title compound (13 mg, 80% yield). 1H NMR (CDCl3) δ 1H NMR (CDCl3) δ 8.63 (m, 1H), 8.58 (m, 1H), 7.6-8.0 (m, 10H), 7.40 (m, 2H), 7.25 (m, 1H), 7.05 (m, 2H), 6.85 (m, 3H), 6.58 (d, J=8.8 Hz, 2H), 6.50 (d, J=11.1 Hz, 2H), 3.7-4.0 (m, 6H), 3.2-3.5 (m, 4H), 2.4-2.8 (m, 3H), 2.95 (m, 1H). LRMS: (calc) 406.1; (found) 407.1 (M+H1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a9a1441df2d144dab639ae7d4bd16594
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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