Hydrochloric Acid → HCID 25066683, compound

HRID 2190214Notes

Reaction equation

HRID 2190214 reaction equation
C(OC([NH:8][C@@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])=[C:28]([O:38][C:39](=[O:43])[CH:40]([CH3:42])[CH3:41])[CH:27]=1)[C:10]([O:12][C@H:13]([CH3:24])[CH2:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17])=[O:11])=O)(C)(C)C.[ClH:44]>O1CCOCC1>[ClH:44].[NH2:8][C@@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])=[C:28]([O:38][C:39](=[O:43])[CH:40]([CH3:42])[CH3:41])[CH:27]=1)[C:10]([O:12][C@H:13]([CH3:24])[CH2:14][O:15][C:16]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:17])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86621598HCID 86621598, compound

Product 1

HCID 25066683HCID 25066683, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(2-methylpropanoyloxy)phenyl]propanoate (1.25 g, 2.0 mmol) was dissolved in 20 mL of 2M 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 (10) (0.66 g, 62% yield) as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.27 (6H, d, J=7.2 Hz), 1.28 (6H, d, J=7.2 Hz), 1.30 (3H, d, J=6.4 Hz), 2.8 (2H, m), 3.17 (1H, dd, J=14.4, 6.8 Hz), 3.20 (1H, dd, J=14.4, 6.4 Hz), 4.25 (1H, t, J=6.8 Hz), 4.31 (1H, dd, J=12.4, 6.4 Hz), 4.47 (1H, dd, J=12, 3.2 Hz), 5.31 (1H, m), 7.12(1H, d, J=8 Hz), 7.14 (1H, d, J=2 Hz), 7.18 (1H, dd, J=8.2 Hz), 7.47 (2H, t, J=7.2 Hz), 7.58 (1H, t, J=7.2 Hz), 8.02 (2H, d, J=7.6 Hz). MS (ESI) m/z 500.16 (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-d261d3bb920d4ffab7df54f664286ac7
Source dataset
uspto-grants-2012_12
Patent number
US08324273B2

Reaction notes

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