m-Chloroperbenzoic acid → HCID 68752815, compound

HRID 1912971Notes

Reaction equation

HRID 1912971 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH:12]1([S:17][CH2:18][C:19]([NH:21][C:22]2[C:31]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[C:34]([CH3:39])[CH:33]=3)=[C:25]3[N:26]=[CH:27][C:28]([CH3:30])=[CH:29][N:24]3[N:23]=2)=[O:20])[CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[CH:12]1([S:17]([CH2:18][C:19]([NH:21][C:22]2[C:31]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[C:34]([CH3:39])[CH:33]=3)=[C:25]3[N:26]=[CH:27][C:28]([CH3:30])=[CH:29][N:24]3[N:23]=2)=[O:20])=[O:6])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68748387HCID 68748387, compound

Product 1

HCID 68752815HCID 68752815, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Solid m-chloroperoxybenzoic acid (30 mg, about 50% titre, 0.10 mmol) was added to an ice-cooled solution of the product from Example 143D (37 mg, 0.093 mmol) in CHCl3 (7 mL). The yellow solution was stirred with ice cooling for 15 minutes, then transferred to a test tube and washed with 20% Na2CO3 (4 mL). The organic phase was concentrated under vacuum, and the residue purified by HPLC (30×100 mm XBridge column eluted with aqueous 0.1 M (NH4)2CO3-MeOH, 80:20-0:100 over 15 min), then by flash chromatography (silica gel eluted with EtOAc-MeOH, 100:0-80:20) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.38-1.54 (m, 1H), 1.64-1.86 (m, 4H), 1.90-2.23 (m, 3H), 2.30 (d, J=1.6 Hz, 3H), 2.38 (s, 3H), 3.34-3.49 (m, 2H), 3.88 (d, J=14.3 Hz, 1H), 7.22-7.31 (m, 1H), 7.34-7.48 (m, 2H), 8.39 (s, 1H), 8.42-8.55 (m, 1H), 9.51 (s, 1H); MS (ESI) m/z 415 (M+H)+.

Workup

  1. customtransferred to a test tube
  2. washwashed with 20% Na2CO3 (4 mL)
  3. concentrationThe organic phase was concentrated under vacuum
  4. customthe residue purified by HPLC (30×100 mm XBridge column eluted with aqueous 0.1 M (NH4)2CO3-MeOH, 80:20-0:100 over 15 min)
  5. washby flash chromatography (silica gel eluted with EtOAc-MeOH, 100:0-80:20)

Sources & evidence

ORD record
ord-7d7451c11ffd4683a84e1d9bff2797be
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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