m-Chloroperbenzoic acid → HCID 90281530, compound

HRID 2170367Notes

Reaction equation

HRID 2170367 reaction equation
[F:1][C:2]1([F:52])[C:6]2[N:7]([CH2:14][C:15]([NH:17][C@H:18]([C:28]3[C:33]([C:34]4[CH:35]=[CH:36][CH:37]=[C:38]5[C:42]=4[N:41]([CH3:43])[N:40]=[C:39]5[NH:44][S:45]([CH3:48])(=[O:47])=[O:46])=[CH:32][N:31]=[C:30](SC)[N:29]=3)[CH2:19][C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=3)=[O:16])[N:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[C:5]=2[C@H:4]2[CH2:51][C@@H:3]12.C1C=C(Cl)C=C(C(OO)=O)C=1.C(N(CC)C(C)C)(C)C.Cl.[CH3:74][C:75]1([OH:79])[CH2:78][NH:77][CH2:76]1>C(Cl)Cl>[F:1][C:2]1([F:52])[C:6]2[N:7]([CH2:14][C:15]([NH:17][C@H:18]([C:28]3[C:33]([C:34]4[CH:35]=[CH:36][CH:37]=[C:38]5[C:42]=4[N:41]([CH3:43])[N:40]=[C:39]5[NH:44][S:45]([CH3:48])(=[O:47])=[O:46])=[CH:32][N:31]=[C:30]([N:77]4[CH2:78][C:75]([OH:79])([CH3:74])[CH2:76]4)[N:29]=3)[CH2:19][C:20]3[CH:21]=[C:22]([F:27])[CH:23]=[C:24]([F:26])[CH:25]=3)=[O:16])[N:8]=[C:9]([C:10]([F:11])([F:13])[F:12])[C:5]=2[C@H:4]2[CH2:51][C@@H:3]12

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 115427813-methylazetidin-3-ol HydrochlorideHCID 90281253HCID 90281253, compound

Product 1

HCID 90281530HCID 90281530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 36B (30 mg, 0.039 mmol) was dissolved in 3 mL of CH2Cl2 and to it was added m-CPBA (17.5 mg, 77%, 0.078 mmol). The reaction mixture was allowed to stir at rt for 20 min. To the reaction mixture was added N,N-diisopropylethylamine (0.2 mL, 0.017 mmol) and 3-methylazetidin-3-ol hydrochloride (34 mg, 0.39 mmol). The reaction mixture was allowed to stir at room temperature for 30 min and then partitioned between EtOAc and brine. The organic layer was separated, washed with brine and dried over Na2SO4 and concentrated. The residue was purified by RP-HPLC eluting with acetonitrile/H2O (with 0.1% TFA) to afford the title product. 1H NMR (400 MHz, methanol-d4) δ 8.53 (dd, 1H), 8.25 (d, 1H), 7.83 (m, 1H), 7.36-6.52 (m, 3H), 6.47-6.22 (m, 2H), 4.85 (m, 3H), 4.40-3.94 (m, 4H), 3.75-2.67 (m, 8H), 2.51 (m, 2H), 1.60 (s, 3H), 1.51-1.23 (m, 1H), 1.18-0.88 (m, 1H). MS (m/z): 808.01 [M+H]+.

Workup

  1. stirringto stir at room temperature for 30 min
  2. custompartitioned between EtOAc and brine
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by RP-HPLC
  8. washeluting with acetonitrile/H2O (with 0.1% TFA)

Sources & evidence

ORD record
ord-7d758da7d7e243ee91daa059c4c13418
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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