m-Chloroperbenzoic acid → HCID 24988246, compound

HRID 1878655Notes

Reaction equation

HRID 1878655 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[S:14][C:13]([O:15][C@@H:16]4[CH:23]5[CH2:24][N:19]6[CH2:20][CH:21]([CH2:25][CH:17]4[CH2:18]6)[CH2:22]5)=[N:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.ClC1C=CC=C(C(OO)=[O:34])C=1>CO>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[S:14][C:13]([O:15][C@@H:16]4[CH:17]5[CH2:18][N+:19]6([O-:34])[CH2:20][CH:21]([CH2:22][CH:23]4[CH2:24]6)[CH2:25]5)=[N:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86621331HCID 86621331, compound

Product 1

HCID 24988246HCID 24988246, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Example 28A (105 mg, 0.30 mmol) in methanol (4 mL) was treated with 3-chloroperbenzoic acid (mCPBA; 70-75%; 71.0 mg, 0.30 mmol; Aldrich) and stirred at ambient temperature for 4 hours. The resulting material was purified by preparative HPLC [Waters® XTerra RP18 column, 5μ, 30×100 mm, flow rate 40 mL/minutes, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide] to afford the title compound: 1H NMR (300 MHz, methanol-D4) δ ppm 1.70-2.02 (m, 2H), 2.10-2.29 (m, 1H), 2.29-2.47 (m, 1H), 2.58-2.78 (m, 2H), 3.57-3.67 (m, 5H), 5.32 (t, J=3.3 Hz, 1H), 6.46 (d, J=3.0 Hz, 1H), 7.26 (d, J=3.3 Hz, 1H), 7.27-7.31 (m, 2H), 7.36-7.42 (m, 1H), 7.66 (d, J=1.3 Hz, 1H), MS (DCI/NH3) m/z=368 (M+H)+.

Workup

  1. customThe resulting material was purified by preparative HPLC [Waters® XTerra RP18 column, 5μ, 30×100 mm, flow rate 40 mL/minutes, 5-95% gradient of acetonitrile in buffer (0.1 M aqueous ammonium bicarbonate

Sources & evidence

ORD record
ord-516680cb5f8b4effa2c7cbd45aa6992c
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

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