Hydrochloric Acid → Methyl (2S)-2-amino-3-(3,5-difluorophenyl)propanoate

HRID 1869716Notes

Reaction equation

HRID 1869716 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@@H:4]([NH:14]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([F:13])[CH:7]=1.C(OC(N[C@@H](CC1C=C(F)C=C(F)C=1)C(OC)=O)=O)C1C=CC=CC=1.Cl.C(=O)(O)[O-].[Na+]>CO>[NH2:14][C@@H:4]([CH2:5][C:6]1[CH:7]=[C:8]([F:13])[CH:9]=[C:10]([F:12])[CH:11]=1)[C:3]([O:2][CH3:1])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 9836527(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propionic acid methyl esterHCID 9968214Methyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-(3,5-difluorophenyl)propanoate

Product 1

HCID 9920793Methyl (2S)-2-amino-3-(3,5-difluorophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid methyl ester (II, EXAMPLE 1, 0.60 g (0.002 moles, 1 equivalent), methanol (20 mL) and hydrochloric acid (3N, 20 mL) are mixed. The mixture is then heated to 500 and stirred until complete as measured by HPLC. When the reaction is complete, the contents are cooled to 20-25° and the pH of the mixture is adjusted to 8 with saturated sodium bicarbonate and then concentrated under reduced pressure. This mixture is extracted with ethyl acetate (2×20 mL) and the combined organic phases are dried over sodium sulfate, filtered and concentrated, HPLC (Retention time=2.89 min; Zorbax RX-C8 acetonitrile/0.05M potassium dihydrogen phosphate, 60/40; 1.0 mL/min, λ=210 nm.

Workup

  1. temperatureThe mixture is then heated to 500
  2. temperaturethe contents are cooled to 20-25°
  3. concentrationconcentrated under reduced pressure
  4. extractionThis mixture is extracted with ethyl acetate (2×20 mL)
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5e18d6142a6a4b908bac9be6c3bb98f4
Source dataset
uspto-grants-2009_12
Patent number
US07638646B2

Reaction notes

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