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

HRID 1360166Notes

Reaction equation

HRID 1360166 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H: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][C@@H: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 11789722N-Boc-(S)-1-amino-2-propanol

Product 1

HCID 86621906(S)-(2-t-butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl esterYield 69.4%

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

1.16 g (6.61 mmol) of (S)-(2-hydroxy-propyl)-carbamic acid t-butyl ester was dissolved in 20 mL of dichloroethane, then 0.66 mL (9.84 mmol) of ethyl diazoacetate was added thereto. 57 mg (0.12 mmol) of rhodium acetate was dropwise added thereto, and then heated to at 80° C. for 2 hour. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give 1.2 g (4.59 mmol) of the title compound in a yield of 69%.

Workup

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

Sources & evidence

ORD record
ord-cb3a68af140f42c8a17e551722efc526
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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