Hydrochloric Acid → Methyl alpha-amino-p-methoxycarbonylmethylphenylacetate

HRID 1289239Notes

Reaction equation

HRID 1289239 reaction equation
C(OC([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O.Cl>C(Cl)Cl.CCOCC.CO.CCOCC>[NH2:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 54316225Methyl alpha-tert-butoxycarbonylamino-p-methoxycarbonylmethyl-phenylacetate

Product 1

HCID 54294376Methyl alpha-amino-p-methoxycarbonylmethylphenylacetate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

To a solution of methyl α-tert-butoxycarbonylamino-p-methoxycarbonylmethyl-phenylacetate (2.86 g, 8.5 mmol) in CH2Cl2 (10 ml) cooled at 0° C. was added 10 ml of TFA. After stirring for 1 hour at room temperature the reaction mixture was evaporated to dryness. The resulting solid was dissolved in ethyl acetate and water and the pH was adjusted to 8 with NaHCO3. After extraction with ethyl acetate the organic layers were washed with brine, dried and evaporated to give a yellow oil. After dissolution of this oil in a mixture of ether:methanol (10:1 v/v) a saturated solution of HCl in ether was added to give, after filtration, methyl α-amino-p-methoxycarbonyl-methylphenylacetate (2.2 g, 96%) as a white solid, m.p. 189.2°-189.6° C.;

Workup

  1. customwas evaporated to dryness
  2. dissolutionThe resulting solid was dissolved in ethyl acetate
  3. extractionAfter extraction with ethyl acetate the organic layers
  4. washwere washed with brine
  5. customdried
  6. customevaporated
  7. customto give a yellow oil
  8. dissolutionAfter dissolution of this oil
  9. additionwas added
  10. customto give
  11. filtrationafter filtration, methyl α-amino-p-methoxycarbonyl-methylphenylacetate (2.2 g, 96%) as a white solid, m.p. 189.2°-189.6° C.

Sources & evidence

ORD record
ord-9ec8b2b771ad4249893cd9784f39e532
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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