HCID 67422368, compound → HCID 46216564, compound

HRID 880707Notes

Reaction equation

HRID 880707 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC=CC=3)=[CH:15][C:14]=2[O:27]CC2C=CC=CC=2)(O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[OH:27])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 67422368HCID 67422368, compound

Product 1

HCID 46216564HCID 46216564, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 g of 3-(2,4-bis(benzyloxy)phenyl)-3-hydroxyazetidine-1-carboxylic acid tert-butyl ester are dissolved in a mixture of 20 ml of ethyl acetate/10 ml of methanol, and then 0.2 g of palladium-on-charcoal at 10% is added. The reaction mixture is stirred for 24 hours under a hydrogen atmosphere. The reaction mixture is filtered and then the residue is chromatographed on silica gel (7/3 heptane/ethyl acetate). 0.16 g of 3-(2,4-dihydroxyphenyl)azetidine-1-carboxylic acid tert-butyl ester is obtained. Yield=28%.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe residue is chromatographed on silica gel (7/3 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-1161839b76a24923848ec50f312e1bc7
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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