1,1'-Carbonyldiimidazole → HCID 11688393, compound

HRID 547283Notes

Reaction equation

HRID 547283 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:13]1([C:18]([C:20]2[CH:21]=[C:22]([C@@H:26]([CH3:30])[C:27](O)=[O:28])[CH:23]=[CH:24][CH:25]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:31][S:32]([NH2:35])(=[O:34])=[O:33].C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH:13]1([C:18]([C:20]2[CH:21]=[C:22]([C@@H:26]([CH3:30])[C:27]([NH:35][S:32]([CH3:31])(=[O:34])=[O:33])=[O:28])[CH:23]=[CH:24][CH:25]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86625605HCID 86625605, compound

Product 1

HCID 11688393HCID 11688393, compoundYield 790%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (0.5 g, 3.06 mmol) was added to a solution of (R)-2-[3-cyclopentanoyl)phenyl]propionic acid (II) (0.68 g, 2.78 mmol) in dry CH2Cl2 (8 mL) and the resulting mixture was left stirring at room temperature for 90 min. Methanesulfonamide (0.26 g, 2.78 mmol) and DBU (0.43 mL, 2.78 mmol) were added and the mixture was left stirring fur further 16 h at room temperature. The organic phase was washed with 0.5N HCl (2×10 mL), with 5% NaH2PO4 (3×10 mL) and with water (2×10 mL). After drying with Na2SO4, solvent was removed under vacuum and the crude was purified by flash chromatography (eluent mixture CH2Cl2/MeOH 95:5). Pure N—[(R)-2-(3-cyclopentanecarbonylphenyl)propionyl]methanesulfonamide 22 was isolated as colourless oil (0.67 g, 2.09 mmol). Yield 790%.

Workup

  1. waitthe resulting mixture was left
  2. waitthe mixture was left
  3. stirringstirring fur further 16 h at room temperature
  4. washThe organic phase was washed with 0.5N HCl (2×10 mL), with 5% NaH2PO4 (3×10 mL) and with water (2×10 mL)
  5. dry with materialAfter drying with Na2SO4, solvent
  6. customwas removed under vacuum
  7. customthe crude was purified by flash chromatography (eluent mixture CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-176ae55669244c2fa53305960e909df6
Source dataset
uspto-grants-2011_05
Patent number
US07939521B2

Reaction notes

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