Isatoic Anhydride → tert-Butyl N-(2-aminobenzoyl)glycinate

HRID 472757Notes

Reaction equation

HRID 472757 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[C:13]([O:17][C:18](=[O:21])[CH2:19][NH2:20])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C=O)C.O>[C:13]([O:17][C:18](=[O:21])[CH2:19][NH:20][C:2](=[O:4])[C:1]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:6])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 8359Isatoic AnhydrideHCID 8471TriethylamineHCID 151417Glycine tert-butyl ester

Product 1

HCID 53432551tert-Butyl N-(2-aminobenzoyl)glycinate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of isatoic anhydride (25 g, 0.15 mol) in DMF (250 ml), glycine tert butyl ester (30.64 g, 0.18 mol) is added, followed by the dropwise addition of triethylamine (52 ml, 0.37 mol) over a period of 30 minutes. The resulting suspension is heated at 50° C. for 3 hours, 60° C. for 30 minutes, then at 70° C. for 30 minutes. The reaction mixture is then allowed to cool to RT and treated with water (300 ml). The resulting solution is stirred at RT for 30 minutes, diluted further with water (200 ml), and the product extracted with EtOAc (2×500 ml). The organic extracts are combined, washed with water (2×300 ml), brine (1×300 ml), dried (MgSO4), filtered, concentrated in vacuo, and dried under vacuum to give the title compound as a peachy white solid.

Workup

  1. temperatureto cool to RT
  2. extractionthe product extracted with EtOAc (2×500 ml)
  3. washwashed with water (2×300 ml), brine (1×300 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ae388195815a435482b27cfda9e85a69
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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