Acetonitrile → HCID 131733538, compound

HRID 2284896Notes

Reaction equation

HRID 2284896 reaction equation
[Cl:1][C:2]1[C:3]([S:18][CH3:19])=[N:4][C:5]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([NH2:17])=[O:16])[CH2:10]2)=[N:6][CH:7]=1.C(#N)C.C1C=C(Cl)C=C(C(OO)=[O:31])C=1.CO.C(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[C:3]([S:18]([CH3:19])=[O:31])=[N:4][C:5]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([NH2:17])=[O:16])[CH2:10]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 70297m-Chloroperbenzoic acidHCID 21584188Chloroform methanolHCID 86729623HCID 86729623, compound

Product 1

HCID 131733538HCID 131733538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 2 (1.9 g, 6.33 mmol) in dichloromethane:acetonitrile (700 mL), m-CPBA (1.19 g, 6.96 mmol) was added and stirred at rt for 1 h. TLC showed completion of starting material and formation of a polar spot (TLC System: 10% methanol/chloroform, (Rf): 0.4). The reaction mixture was concentrated, diluted with dichloromethane (30 ml), and washed with saturated sodium bicarbonate solution (20 mL) and water (15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude compound was purified by silica gel column chromatography with 1 to 1.5% methanol in chloroform as eluents to afford Intermediate 3 as colorless gummy solid. (1.4 g, 70%). MS m/z: 317.1 (ES+, M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with dichloromethane (30 ml)
  3. washwashed with saturated sodium bicarbonate solution (20 mL) and water (15 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude compound was purified by silica gel column chromatography with 1 to 1.5% methanol in chloroform as eluents

Sources & evidence

ORD record
ord-bc227b52eeac403eabebb3fb93e91ebc
Source dataset
uspto-grants-2015_09
Patent number
US09145387B2

Reaction notes

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