Hydrochloric Acid → HCID 57462282, compound

HRID 2190107Notes

Reaction equation

HRID 2190107 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:27]C(OC(C)(C)C)=O)[C:11]([O:13][C@H:14]([CH3:26])[C@H:15]([O:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH3:16])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[ClH:35]>O1CCOCC1>[ClH:35].[NH2:27][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]([CH3:26])[C@H:15]([O:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])[CH3:16])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60207251HCID 60207251, compound

Product 1

HCID 57462282HCID 57462282, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R,2R)-1-Methyl-2-phenylcarbonyloxypropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (1.8 g, 2.7 mmol) was dissolved in 40 mL of 4M HCl in dioxane. The mixture was stirred at room temperature for 30 min. The dioxane was evaporated completely under reduced pressure. The resulting a 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 crystallized. The white, crystalline solid was collected and dried under vacuum to afford 1.0 g (87% yield) of the title compound (1). 1H NMR (400 MHz, CD3OD): δ 1.12 (d, J=6 Hz, 3H), 1.24 (d, J=6 Hz, 3H), 2.85 (dd, J=14, 8 Hz, 1H), 3.02 (dd, J=14, 5.2 Hz, 1H), 4.15 (t, J=5.6 Hz, 1H), 5.06 (m, 2H), 6.46 (dd, J=8, 2 Hz, 1H), 6.61 (d, J=2 Hz, 1H), 6.65 (d, J=8 Hz, 1H), 7.54 (t, J=7.6 Hz, 2H), 7.65 (t, J=7.6 Hz, 1H), 7.90 (m, 2H). MS (ESI) m/z 374.11 (M+H)+ and 372.08 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-d6cf4a024e3746cbb68e00dc201f09e3
Source dataset
uspto-grants-2012_12
Patent number
US08324272B2

Reaction notes

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