Methyl Anthranilate → HCID 24807790, compound

HRID 1264904Notes

Reaction equation

HRID 1264904 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:28]([O:37][CH3:38])(=[O:36])[C:29]1[C:30](=[CH:32][CH:33]=[CH:34][CH:35]=1)[NH2:31]>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH3:38][O:37][C:28](=[O:36])[C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH:31][C:13](=[O:15])[CH2:12][NH:11][C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:10]

Participants

7

Reactant 3

HCID 8635Methyl AnthranilateHCID 14349BenzyloxycarbonylglycineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 24807790HCID 24807790, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of N-α-Cbz-glycine (2.0 g, 9.56 mmol) in tetrahydrofuran (20 mL) was added 1,1′-carbonyldiimidazole (1.64 g, 10.13 mmol), followed 2 h later by methyl anthranilate (1.28 g, 8.47 mmol). After stirring overnight the tetrahydrofuran was removed in vacuo and the residue was redissolved in ethyl acetate, washed with 10% aqueous hydrochloric acid (2×), saturated aqueous sodium hydrogen carbonate (2×), dried (MgSO4) and concentrated to give an oily residue which was subjected to silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 30:70, v/v→Ethyl acetate] to give the title benzoate (1) (0.31 g, 11%) as a white solid:

Workup

  1. customwas removed in vacuo
  2. dissolutionthe residue was redissolved in ethyl acetate
  3. washwashed with 10% aqueous hydrochloric acid (2×), saturated aqueous sodium hydrogen carbonate (2×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give an oily residue which

Sources & evidence

ORD record
ord-82db2de85e9f4a8bbf1490ac1bdf643d
Source dataset
uspto-grants-2003_04
Patent number
US06545005B1

Reaction notes

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