Hydrochloric Acid → HCID 86621599, compound

HRID 1171237Notes

Reaction equation

HRID 1171237 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[C:28]([O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])[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:7])([CH3:4])([CH3:3])[CH3:2].[ClH:46]>O1CCOCC1>[ClH:46].[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33](=[O:38])[C:34]([CH3:36])([CH3:35])[CH3:37])=[C:28]([O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])[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:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25066684HCID 25066684, compound

Product 1

HCID 86621599HCID 86621599, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R)-1-Methyl-2-phenylcarbonyloxyethyl(2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(2,2-dimethylpropanoyloxy)phenyl]propanoate (13) (1.03 g, 1.64 mmol) was dissolved in 20 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 (12) (0.851 g, 98% yield) as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.30 (3H, d, J=6.4 Hz), 1.33 (9H, s), 1.34 (9H, s), 3.13 (1H, dd, J=14.4, 6.8 Hz), 3.20 (1H, dd, J=14.4, 6.4 Hz), 4.22 (1H, t, J=6.8 Hz), 4.32 (1H, dd, J=12.4, 6.4 Hz), 4.49 (1H, dd, J=12, 3.2 Hz), 5.33 (1H, m), 7.10 (1H, d, J=8 Hz), 7.11 (1H, d, J=2 Hz), 7.17 (1H, dd, J=2, 8 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 528.14 (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-308f7ce00f364f2aa1664261339e3e25
Source dataset
uspto-grants-2010_11
Patent number
US07829592B2

Reaction notes

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