Ethyl diazoacetate → (2-t-Butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl ester

HRID 1360162Notes

Reaction equation

HRID 1360162 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-]>ClC(Cl)C.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][O:11][CH:9]([CH3:10])[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:12])[CH3:20]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 9920508tert-butyl N-(2-hydroxypropyl)carbamate

Product 1

HCID 86621905(2-t-Butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl esterYield 50.9%

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

500 mg (2.85 mmol) of (2-hydroxy-propyl)-carbamic acid t-butyl ester was dissolved in 10 mL of dichloroethane, then 0.44 mL (4.24 mmol) of ethyl diazoacetate was added thereto. 38 mg (0.085 mmol) of rhodium acetate was added to the reaction and then heated to 80° C. for 2 hours. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give 381 mg (1.45 mmol) of the title compound in a yield of 50%.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-56f23c32cfaf48b28aa22932f09fbbc6
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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