Methanol → HCID 86630336, compound

HRID 604245Notes

Reaction equation

HRID 604245 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:23])[CH2:6][NH:7][C:8](=[O:22])[CH2:9][NH:10][C:11](=[O:21])[C@H:12]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[NH2:13])[CH3:3].C(N(CC)C(C)C)(C)C.[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38](Cl)=[O:39].CO>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:23])[CH2:6][NH:7][C:8](=[O:22])[CH2:9][NH:10][C:11](=[O:21])[C@H:12]([CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[NH:13][C:38]([C:34]1[O:33][CH:37]=[CH:36][CH:35]=1)=[O:39])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 66638003HCID 66638003, compound

Product 1

HCID 86630336HCID 86630336, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 90.1 mg (0.258 mmol) of β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester hydrochloride in methylenechloride (1 mL), 100.0 mg (0.774 mmol) of N,N-diisopropylethylamine and 37.2 mg (0.285 mmol) of 2-furoyl chloride were added with stirring under ice cooling and the reaction mixture was stirred for 0.5 hour. Methanol (0.2 mL) was added and the reaction mixture was stirred at room temperature, and then concentrated under reduced pressure. Chloroform (25 mL) was added to the residue, and then the mixture was washed with 0.5M hydrochloric acid (3×5 mL) and 5% aqueous sodium hydrogencarbonate solution (3×5 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, whereby 127 mg of the crude product was obtained. The crude product was purified by silica gel column chromatography [silica gel 7.5 g, chloroform, methanol-chloroform (1:100)], to give 103.2 mg of 2-furoyl-β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester as a colorless oil (yield 98%)

Workup

  1. stirringthe reaction mixture was stirred for 0.5 hour
  2. stirringthe reaction mixture was stirred at room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionChloroform (25 mL) was added to the residue
  5. washthe mixture was washed with 0.5M hydrochloric acid (3×5 mL) and 5% aqueous sodium hydrogencarbonate solution (3×5 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customwhereby 127 mg of the crude product was obtained
  9. customThe crude product was purified by silica gel column chromatography [silica gel 7.5 g, chloroform, methanol-chloroform (1:100)]

Sources & evidence

ORD record
ord-1d8d64bfb6d34c72b1cb8b6167f8b177
Source dataset
uspto-grants-2011_03
Patent number
US07910556B2

Reaction notes

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