Hydrochloric Acid → (alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid

HRID 716528

Reaction equation

HRID 716528 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[CH3:17][O:18][C:19](Cl)=[O:20].Cl>O1CCCC1.O>[CH3:17][O:18][C:19]([NH:11][C@H:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:8]([OH:10])=[O:9])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 70134Phenylglycine, D-HCID 516892Sodium Bicarbonate

Product 1

HCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

D-(−)-α-Phenylglycine (0.165 mmol) was dissolved in tetrahydrofuran (500 mL), followed by the addition of NaHCO3 (0.496 mmol) in water (500 mL), and then the addition of methylchloroformate (0.182 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. The mixture was acidified to pH=3 with HCl (1N) and the volatile was concentrated in vacuo. The aqueous layer was extracted with ethyl acetate and the organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give compound 31 as a pale yellow solid in 80% yield. MS (ESI, EI+) m/z=209 (MH+).

Workup

  1. concentrationthe volatile was concentrated in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d29ace45e3554fff8245c4da1b951547
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Linked notes

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