Hydrochloric Acid → HCID 25066681, compound

HRID 1171234Notes

Reaction equation

HRID 1171234 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:8]=[C:9]([CH2:19][C@H:20]([NH:36]C(OC(C)(C)C)=O)[C:21]([O:23][C@H:24]([CH3:35])[CH2:25][O:26][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:28])=[O:22])[CH:10]=[CH:11][C:12]=1[O:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].[ClH:44]>O1CCOCC1>[ClH:44].[NH2:36][C@@H:20]([CH2:19][C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([O:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:8]=1)[C:21]([O:23][C@H:24]([CH3:35])[CH2:25][O:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86621596HCID 86621596, compound

Product 1

HCID 25066681HCID 25066681, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R)-1-Methyl-2-phenylcarbonyloxyethyl(2S)-3-[3,4-bis(ethoxycarbonyloxy)phenyl]-2-[(tert-butoxy)carbonylamino]propanoate (7) (1.6 g, 2.65 mmol) was dissolved in 10 mL of 4M HCl in dioxane. The reaction mixture was stirred at room temperature for 60 min. Dioxane was completely evaporated under reduced pressure. The resulting white solid was dissolved in water (15 mL) and washed with methyl tert-butyl ether. The aqueous phase was collected and mixed with acetonitrile (10 mL). Lyophilization gave the title compound (6) (1.4 g, 100% yield) as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.31 (3H, d, J=6.8 Hz), 1.35 (6H, t, J=6.8 Hz), 3.23 (1H, d, J=3.2 Hz), 3.25 (1H, d, J=4 Hz), 4.28 (4H, q, 6.8 Hz), 4.31 (1H, dd, J=14, 5.6 Hz), 4.38 (1H, t, J=7.2 Hz), 4.49 (1H, dd, J=12, 3.2 Hz), 5.35 (1H, m), 7.24 (1H, d, J=2 Hz), 7.27 (1H, d, J=8 Hz), 7.28 (1H, d, J=2 Hz), 7.48 (2H, t, J=7.2 Hz), 7.61 (1H, t, J=7.2 Hz), 8.02 (2H, d, J=7.6 Hz). MS (ESI) m/z 504.16 (M+H)+.

Workup

  1. customDioxane was completely evaporated under reduced pressure
  2. dissolutionThe resulting white solid was dissolved in water (15 mL)
  3. washwashed with methyl tert-butyl ether
  4. customThe aqueous phase was collected
  5. additionmixed with acetonitrile (10 mL)

Sources & evidence

ORD record
ord-08930e741fd643999464b3488eaa2300
Source dataset
uspto-grants-2010_11
Patent number
US07829592B2

Reaction notes

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