18-Crown-6 → HCID 90411955, compound

HRID 1521931Notes

Reaction equation

HRID 1521931 reaction equation
C(OC([NH:8][C:9]1[C:14]([C:15]#[C:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[C:13]([Cl:30])[CH:12]=[CH:11][N:10]=1)=O)(C)(C)C.CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:30][C:13]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:8][C:16]([CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]3)=[CH:15][C:14]=12

Participants

6

Reactant 3

HCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 131733112HCID 131733112, compound

Product 1

HCID 90411955HCID 90411955, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of product of Example 1E (250 mg, 0.573 mmol) in toluene (5 mL) was added potassium tert-butoxide (161 mg, 1.434 mmol) followed by 18-crown-6 (15 mg, 0.057 mmol) and the mixture was heated at 65° C. for 12 hours. The mixture was dissolved in ethyl acetate (25 mL), washed with water and brine, and dried over anhydrous sodium sulfate. Filtration followed by concentration of the filtrate afforded crude product which was purified by column chromatography (silica gel, 40% ethyl acetate in hexane) to afford the title compound. LCMS: 336.0 (M+H-Boc)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration
  4. customafforded crude product which
  5. customwas purified by column chromatography (silica gel, 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d234ae06d0074722ae4ab0ad50ba38a3
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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