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

HRID 23217Notes

Reaction equation

HRID 23217 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 50° 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 50°
  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-1f4cdcf0cc974bdca7f442940b6aaf69
Source dataset
uspto-grants-2005_02
Patent number
US06849750B2

Reaction notes

Loading…