m-Chloroperbenzoic acid → HCID 87666749, compound

HRID 351396Notes

Reaction equation

HRID 351396 reaction equation
FC(F)(F)C(O)=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][CH:45]=1)[C:12]([NH:14][C@H:15]1[CH2:19][CH2:18][N:17]([C@H:20]2[CH2:25][CH2:24][C@@H:23]([N:26]([CH:28]([CH3:30])[CH3:29])[CH3:27])[CH2:22][C@H:21]2[CH2:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:16]1=[O:42])=[O:13].ClC1C=C(C=CC=1)C(OO)=O>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][CH:45]=1)[C:12]([NH+:14]([O-:4])[C@H:15]1[CH2:19][CH2:18][N:17]([C@H:20]2[CH2:25][CH2:24][C@@H:23]([N:26]([CH:28]([CH3:30])[CH3:29])[CH3:27])[CH2:22][C@H:21]2[CH2:31][S:32]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)(=[O:33])=[O:34])[C:16]1=[O:42])=[O:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69038604HCID 69038604, compound

Product 1

HCID 87666749HCID 87666749, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 86 (13.6 mg) in CH2Cl2 (1.5 mL) was cooled to 0° C., then 3-chloroperoxybenzoic acid (77%, 10 mg) was added portion-wise. The mixture was stirred for 1.25 h, then diluted with CH2Cl2 (400 mL), washed with satd NaHCO3 (3×100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by semi-preparative HPLC to give the title compound (6.8 mg, 57%) as a white solid after lyophilization from MeCN/aqueous TFA. ESI MS m/z 596 [C28H35Cl2N3O5S+H]+.

Workup

  1. washwashed with satd NaHCO3 (3×100 mL) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-9ff24cc49aa94ea3ba2bee832871f00d
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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