Hydrochloric Acid → HCID 86643594, compound

HRID 2381021Notes

Reaction equation

HRID 2381021 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:26]C(OC(C)(C)C)=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[C:8]([O:20][C:21](=[O:25])[NH:22][CH2:23][CH3:24])[CH:7]=1.[ClH:35]>O1CCOCC1.CO.[H][H].[C].[Pd]>[Cl-:35].[CH2:23]([NH:22][C:21]([O:20][C:8]1[CH:7]=[C:6]([CH2:5][C@H:4]([NH3+:26])[C:3]([O:2][CH3:1])=[O:34])[CH:11]=[CH:10][C:9]=1[OH:12])=[O:25])[CH3:24]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 68726640HCID 68726640, compound

Product 1

HCID 86643594HCID 86643594, compound

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

(S)-3-(4-Benzyloxy-3-ethylcarbamoyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (220 mg) was dissolved in 4M HCl in dioxane (3 ml) and the solution was left at room temperature for ca 2 hr. Evaporation of solvent gave a white solid which was redissolved in methanol (5 ml) and hydrogenated at 1 atmosphere of hydrogen gas over 5% palladium-carbon (44 mg). After stirring overnight at room temperature the catalyst was removed by filtration and washed with methanol. Evaporation of the filtrate gave a gum which was crystallised from methanol-ether. (S)-2-(3-Ethylcarbamoyloxy-4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl-ammonium chloride was obtained as a white solid, 110 mg; NMR (500 MHz, d6 DMSO) 1.07 (3H, t J 7), 2.94-3.09 (4H, m), 3.67 (3H, s), 4.18 (1H, t J 6), 6.84 (3H, br s), 7.56 (1H, t J 5.5), 8.43 (ca 3H, br s), 9.55 (1H, s); HPLC/MS retention time 3.41 min, m/z 283 (MH+).

Workup

  1. waitthe solution was left at room temperature for ca 2 hr
  2. customEvaporation of solvent
  3. customgave a white solid which
  4. customwas removed by filtration
  5. washwashed with methanol
  6. customEvaporation of the filtrate
  7. customgave a gum which
  8. customwas crystallised from methanol-ether

Sources & evidence

ORD record
ord-6e1e18aba5df4caeb4d8981741a3aff4
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

Loading…