Cyclopentane, methylene- → N-CBZ-O-(1-methylcyclopentyl)-L-serine methylester

HRID 653387

Reaction equation

HRID 653387 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:16][OH:17])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[CH2:19]=[C:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])O.[Na+]>ClCCl.S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:16][O:17][C:20]1([CH3:19])[CH2:24][CH2:23][CH2:22][CH2:21]1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

6

Reactant 3

HCID 73714Cyclopentane, methylene-HCID 516892Sodium BicarbonateHCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

Product 1

HCID 15594942N-CBZ-O-(1-methylcyclopentyl)-L-serine methylesterYield 78%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

N-CBZ-L-serine methyl ester (3.15 g) was dissolved in 40 ml of dichloromethane at 0° C. under argon. Methylenecyclopentane (20 ml) was added, followed by 16 drops of concentrated sulfuric acid. The contents of the vessel were stirred at room temperature overnight then poured into dilute aqueous sodium hydrogen carbonate and extracted with chlorofrom (2×30 ml). The organic layer was dried over sodium sulfate and evaporated. The residual oil was chromatographed on silica gel with 50/50 petroleum ether/diethyl ether to give an oil (78% yield). The product, N-CBZ-O-(1-methylycyclopentyl)-L-serine methyl ester, was confirmed by NMR spectroscopy.

Workup

  1. extractionextracted with chlorofrom (2×30 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated
  4. customThe residual oil was chromatographed on silica gel with 50/50 petroleum ether/diethyl ether

Sources & evidence

ORD record
ord-6f5f8e0ae3f944828dc03e7b61083fa2
Source dataset
uspto-grants-1987_06
Patent number
US04676989

Linked notes

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