Hydrochloric Acid → (1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate Hydrochloride

HRID 1698470Notes

Reaction equation

HRID 1698470 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:26]C(OC(C)(C)C)=O)[C:11]([O:13][C@H:14]([CH3:25])[CH2:15][O:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[ClH:34]>O1CCOCC1>[ClH:34].[NH2:26][C@@H:10]([CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1)[C:11]([O:13][C@H:14]([CH3:25])[CH2:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60207245(1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate

Product 1

HCID 60207241(1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate HydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R)-1-Methyl-2-phenylcarbonyloxyethyl(2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (1.87 g, 4 mmol) was dissolved in 40 mL of 4M HCl in dioxane. The resulting mixture was stirred at room temperature for 30 min. Dioxane was evaporated completely under reduced pressure. The resulting white solid was dissolved in acetonitrile (5 mL), and ether added until the solution became slightly cloudy. The solution was refrigerated overnight and the product was crystallized. The white crystalline solid was collected and dried under vacuum to afford 1.5 g (93%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 1.35 (d, J=6.4 Hz, 3H), 3.01 (dd, J=6.8, 14.4 Hz, 1H), 3.08 (dd, J=6.4, 14.4 Hz, 1H), 4.19 (t, J=6.4 Hz, 1H), 4.34 (dd, J=6, 12.4 Hz, 1H), 4.49 (dd, J=2.8, 12.4 Hz, 1H), 5.35 (m, 1H), 6.55 (dd, J=2, 8 Hz, 1H), 6.66 (d, J=2 Hz, 1H), 6.71 (d, J=8 Hz, 1H), 7.48 (t, J=7.2 Hz, 2H), 7.61 (t, J=7.2 Hz, 1H), 8.02 (d, J=7.6 Hz, 2H). MS (ESI) m/z 360.16 (M+H)+ and 358.13 (M−H)−.

Workup

  1. customDioxane was evaporated completely under reduced pressure
  2. dissolutionThe resulting white solid was dissolved in acetonitrile (5 mL)
  3. additionether added until the solution
  4. waitThe solution was refrigerated overnight
  5. customthe product was crystallized
  6. customThe white crystalline solid was collected
  7. customdried under vacuum

Sources & evidence

ORD record
ord-cba6b463f2a5456dbab5149cdfa6023f
Source dataset
uspto-grants-2012_04
Patent number
US08163958B2

Reaction notes

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