Dichloromethane → Butyl α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-furanacetate

HRID 1973486Notes

Reaction equation

HRID 1973486 reaction equation
[CH2:1]([O:5][C:6](=[O:20])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4].[O:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.C(Cl)Cl>B(F)(F)F.CCOCC.C(OCC)(=O)C>[CH2:1]([O:5][C:6](=[O:20])[CH:7]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C:22]1[O:21][CH:25]=[CH:24][CH:23]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6344Dichloromethane3×HCID 8029FuranHCID 20312395HCID 20312395, compound

Product 1

HCID 54559425Butyl α-[[(1,1-dimethylethoxy)carbonyl]amino]-2-furanacetate

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.6 g. (0.006 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester and 0.7 g. (0.01 mol.) of redistilled furan in 75 ml. of methylene chloride was cooled to -78° and four drops of boron trifluoride etherate was added with stirring. The reaction mixture was warmed to room temperature and left for three hours. Chromatography on silica gel with methylene chloride and methylene chloride containing increasing amounts of ethyl acetate gave the title compound.

Sources & evidence

ORD record
ord-c199a5d5d2354edb9410bbaa6249cafd
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

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