Hydrochloric Acid → HCID 131720725, compound

HRID 964615Notes

Reaction equation

HRID 964615 reaction equation
C([NH:4][C@@:5]([CH3:17])([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:6]([OH:8])=[O:7])(=O)C.[ClH:18]>>[ClH:18].[NH2:4][C@@:5]([CH3:17])([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:6]([OH:8])=[O:7]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 54171914HCID 54171914, compound

Product 1

HCID 131720725HCID 131720725, compoundYield 92%

Procedure

A suspension of (S)-(+)-α-acetamido-4-methoxy-α-methylbenzeneacetic acid (30 g, 126 mmol) in 4N HCl (300 mL) was refluxed for 2 hours and evaporated in vacuo to dryness. The residue was repeatedly dissolved in EtOH and evaporated again to dryness (4 liters of EtOH were used). The final solid was washed with tert-butyl methyl ether (4×100 mL) and finally with acetone (2×125 mL), dried in vacuo at 40° C. in presence of P2O5 to yield 26.92 g of (S)-α-amino-4-methoxy-α-methylbenzeneacetic acid, hydrochloride salt (92%, mp: >260° C.). αD : 70.4° (1N HCl, c=1).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customevaporated in vacuo to dryness
  3. dissolutionThe residue was repeatedly dissolved in EtOH
  4. customevaporated again to dryness (4 liters of EtOH were used)
  5. washThe final solid was washed with tert-butyl methyl ether (4×100 mL) and finally with acetone (2×125 mL)
  6. dry with materialdried in vacuo at 40° C. in presence of P2O5

Sources & evidence

ORD record
ord-75684e50eba14633a9e5b2efe7bf6dcf
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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