Hydrochloric Acid → HCID 25066683, compound

HRID 1171236Notes

Reaction equation

HRID 1171236 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-0f91969822294c9b93c1e0fccb45902e
Source dataset
uspto-grants-2010_11
Patent number
US07829592B2

Reaction notes

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