Ethyl Acetate → Ethyl 1-{[(tert-butoxy)carbonyl]amino}-3-hydroxycyclobutane-1-carboxylate

HRID 1045115Notes

Reaction equation

HRID 1045115 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:9][CH:8]([O:10]CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2].C(OCC)(=O)C.[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:7][CH:8]([OH:10])[CH2:9]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14728571Ethyl 3-(Benzyloxy)-1-(Boc-amino)cyclobutanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 14728572Ethyl 1-{[(tert-butoxy)carbonyl]amino}-3-hydroxycyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 1-(N-(t-butoxycarbonyl)amino)-3-benzyloxy-cyclobutane-1-carboxylic acid ethyl ester synthesized as above is dissolved in an alcohol solvent such as ethanol or an acetate ester solvent such as ethyl acetate ester, and palladium-on-activated carbon (amount: 10 w/w % or more relative to the substrate) is added to the solution in an atmosphere of hydrogen to allow them to react under stirring at room temperature. The reaction solution is then filtered through Celite, and the filtrate is concentrated and purified to yield 1-(N-(t-butoxycarbonyl)amino)-3-hydroxy-cyclobutane-1-carboxylic acid ethyl ester (Step 4).

Workup

  1. customto react
  2. filtrationThe reaction solution is then filtered through Celite
  3. concentrationthe filtrate is concentrated
  4. custompurified

Sources & evidence

ORD record
ord-ad638db0bd574ebd8d6095734348d288
Source dataset
uspto-grants-2013_10
Patent number
US08563771B2

Reaction notes

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