N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → HCID 68507383, compound

HRID 1715190Notes

Reaction equation

HRID 1715190 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=[N:18][C:17]2[N:20]([OH:23])N=N[C:16]=2[CH:15]=1.NC1C=CON=1>C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH2:10][C:11](=[O:13])[NH:18][C:17]1[CH:16]=[CH:15][O:23][N:20]=1)([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 181649HOAtHCID 18102163-Isoxazolamine

Product 1

HCID 68507383HCID 68507383, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising BOC-β-alanine (1 g, 5.29 mmol), WSCD (0.985 g, 6.34 mmol) and HOAT (0.216 g, 1.59 mmol) in DCM is treated with 3-aminoisoxazole (0.43 ml, 5.81 mmol) and left stirring overnight. The resulting mixture is washed with water, brine, dried (MgSO4) and concentrated in vacuo. The crude product is purified by chromatography on silica eluting with EtOAc to afford the title compound as a white solid.

Workup

  1. waitleft
  2. washThe resulting mixture is washed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by chromatography on silica eluting with EtOAc

Sources & evidence

ORD record
ord-422a3b659ce9443cb781d724358583fa
Source dataset
uspto-grants-2010_09
Patent number
US07799810B2

Reaction notes

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