Methanol → HCID 86630336, compound

HRID 1093922Notes

Reaction equation

HRID 1093922 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 thus obtained β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester hydrochloride (90.1 mg, 0.258 mmol) in methylene chloride (1 mL) with stirring under ice cooling, N,N-diisopropylethylamine (100.0 mg, 0.774 mmol) and 2-furoyl chloride(37.2 mg, 0.285 mmol) were added and the reaction mixture was stirred for 0.5 hour. After addition of methanol (0.2 mL), the reaction mixture was stirred under room temperature and concentrated under vacuum. To the residue, chloroform (25 mL) was added and the solution was washed with 0.5 M hydrochloric acid (3×5 mL) and 5% aqueous sodium hydrogen carbonate solution (3×5 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum to obtain a crude product (127 mg). The crude product was purified by silica-gel column chromatography [silica gel 7.5 g, chloroform ->methanol-chloroform (1:100)] to obtain 2-furoyl-β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester (103.2 mg) as a colorless oily material (yield 98%).

Workup

  1. stirringthe reaction mixture was stirred under room temperature
  2. concentrationconcentrated under vacuum
  3. additionTo the residue, chloroform (25 mL) was added
  4. washthe solution was washed with 0.5 M hydrochloric acid (3×5 mL) and 5% aqueous sodium hydrogen carbonate solution (3×5 mL)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto obtain a crude product (127 mg)
  8. 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-d36838c472244f8da1b2b89e79d5caa0
Source dataset
uspto-grants-2012_03
Patent number
US08133864B2

Reaction notes

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