m-Chloroperbenzoic acid → 4-[8-(4-Methanesulfonyl-phenyl)-quinolin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester

HRID 1864182Notes

Reaction equation

[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:23]3[C:18](=[C:19]([C:24]4[CH:29]=[CH:28][C:27](SC)=[CH:26][CH:25]=4)[CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH:32]1C=C(Cl)C=C(C(OO)=O)C=1.[S:43](=[O:46])(O)[O-:44].[Na+]>C(Cl)Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([O:13][C:14]2[C:23]3[C:18](=[C:19]([C:24]4[CH:29]=[CH:28][C:27]([S:43]([CH3:32])(=[O:46])=[O:44])=[CH:26][CH:25]=4)[CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 25 mL round-bottomed flask immersed in an ice-bath was placed a stir bar and Compound F2 (16 mg, 0.037 mmol) in CH2Cl2 (5 mL). A solution of mCPBA (19 mg, 0.081 mmol) dissolved in CH2Cl2 (1 mL) was added at 0° C. The mixture was stirred at 0° C. for 30 min. A solution of sodium bisulfite was added. The organic phase was separated, dried and concentrated to give the crude product. The crude was purified by HPLC. 1H NMR (CDCl3, 400MHz) δ 1.29 (d, 6H), 2.04 (m, 2H), 2.20 (m, 2H), 3.16 (s, 3H), 3.59 (m, 2H), 3.85 (m, 2H), 4.97 (m, 1H), 5.14 (m, 1H), 7.23 (s, 1H), 7.66 (d, 2H), 7.92 (m, 2H), 8.12 (d, 2H), 8.48 (d, 1H), 9.08 (d, 1H). Exact mass calculated for C25H28N2O5S 468.17, found 469.2 (MH+).

Workup

customIn a 25 mL round-bottomed flask immersed in an ice-bath
additionwas added at 0° C
customThe organic phase was separated
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-99410eec7dc84c999ac461bd3d030444
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625906B2

Reaction notes

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