m-Chloroperbenzoic acid → HCID 58333566, compound

HRID 2066847Notes

Reaction equation

HRID 2066847 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH:28]4[S:33][CH2:32][CH2:31][CH2:30][S:29]4)=[CH:23][C:22]=3[F:34])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:43])C=1>C(Cl)Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH:28]4[S:33][CH2:32][CH2:31][CH2:30][S:29]4=[O:43])=[CH:23][C:22]=3[F:34])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 87350295HCID 87350295, compound

Product 1

HCID 58333566HCID 58333566, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

21a (55 mg) was dissolved in 0.5 mL of DCM and cooled to −78° C. mCPBA (24 mg, 1 eq) in 1 mL of DCM was added and the mixture was stirred at room temperature for 2 days. The solution was washed with aqueous Na2CO3 twice then with water and the crude material obtained was purified on preparative HPLC to give 21-1 as a 15:85 mixture of diastereoisomers: LC-MS 530.2 (MH), tR=5.58 (Method 5). EC50: 143 nM.

Workup

  1. additionwas added
  2. washThe solution was washed with aqueous Na2CO3 twice

Sources & evidence

ORD record
ord-ef5b78d5261249cdabaade7841c25df5
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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