Hydrochloric Acid → 2-(2-Benzyloxycarbonylamino-acetylamino)-benzoic Acid

HRID 1264905Notes

Reaction equation

HRID 1264905 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:26])[CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].Cl>O.O1CCOCC1>[CH2:19]([O:18][C:16]([NH:15][CH2:14][C:13]([NH:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]([OH:27])=[O:4])=[O:26])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 24807790HCID 24807790, compound

Product 1

HCID 107113492-(2-Benzyloxycarbonylamino-acetylamino)-benzoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide (55 mg, 1.32 mmol) in water (0.8 mL), was added to a solution of the benzoate (1) (300 mg, 0.88 mmol) in dioxane (4 mL). After stirring overnight, the reaction mixture was concentrated at 40° C. to give a viscous oil, which was treated with 10% aqueous hydrochloric acid (3 mL), with the resulting emulsion formed being extracted with ethyl acetate (4×). The organic phases were combined, dried (MgSO4) and concentrated to give the title benzoic acid (2) quantitatively as a white solid:

Workup

  1. concentrationthe reaction mixture was concentrated at 40° C.
  2. customto give a viscous oil, which
  3. customformed
  4. extractionbeing extracted with ethyl acetate (4×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c4b8ae7c7e3494ca403ff1340c782c7
Source dataset
uspto-grants-2003_04
Patent number
US06545005B1

Reaction notes

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