Toluene → 2-(((Benzyloxy)carbonyl)amino)-4-carbamoylbutanoic acid

HRID 2088329Notes

Reaction equation

HRID 2088329 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].C(=O)(O)[O-].[Na+].C1(C)C=CC=CC=1.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(OCC)(=O)C>[CH2:27]([O:26][C:24]([NH:1][CH:2]([CH2:3][CH2:4][C:5](=[O:7])[NH2:6])[C:8]([OH:10])=[O:9])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5961L-GlutamineHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 3024262-(((Benzyloxy)carbonyl)amino)-4-carbamoylbutanoic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Glutamine (36.5 g, 0.25 mol) was stirred with 1M sodium bicarbonate (750 ml) and toluene (200 ml). Benzyl chloroformate (50 ml, 59.75 g, 0.35 mol, 1.4 equiv.) was added drop-wise over 20 min. and the resulting mixture was stirred under nitrogen at room temperature overnight. Ethyl acetate (400 ml) was added and phases were separated. The organic phase was extracted with water (50 ml) and discarded. The aqueous phase was acidified with 6N hydrochloric acid and extracted with ethyl acetate (2×600 ml). The combined extracts were washed with water (100 ml) and stripped. The residue was dried in a vacuum oven (50° C.) to produce (1) (64 g, 91.4%).

Workup

  1. customphases were separated
  2. extractionThe organic phase was extracted with water (50 ml)
  3. extractionextracted with ethyl acetate (2×600 ml)
  4. washThe combined extracts were washed with water (100 ml)
  5. customThe residue was dried in a vacuum oven (50° C.)

Sources & evidence

ORD record
ord-adddea8a8c82442eba7a51b230140b1c
Source dataset
uspto-grants-2013_05
Patent number
US08435956B2

Reaction notes

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