Water → HCID 68589889, compound

HRID 472753Notes

Reaction equation

HRID 472753 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13].Cl[C:16]([O:19]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl.O>O1CCOCC1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][N:5]1[CH2:6][C:7]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:13][C:16]1=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 94429TriphosgeneHCID 65440269(2-Amino-benzylamino)-acetic acid methyl ester

Product 1

HCID 68589889HCID 68589889, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(2-Amino-benzylamino)-acetic acid methyl ester (0.50 g, 2 mmol) and bis(trichloromethyl)carbonate (0.54 g, 2 mmol) are dissolved in dioxane (5 ml) and stirred at RT for 24 hours. The reaction mixture is treated with water and extracted with EtOAc, the organic phase is dried over MgSO4, filtered and is concentrated in vacuo. Purification by flash column chromatography on silica, eluting with DCM:MeOH (10:1) affords the title compound. [M+H]+ 221.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. concentrationis concentrated in vacuo
  5. customPurification by flash column chromatography on silica
  6. washeluting with DCM:MeOH (10:1)

Sources & evidence

ORD record
ord-ff2e07721b4a48c8a7fdcf452ab50b8a
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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