Hydrochloric Acid → HCID 87173151, compound

HRID 1514825Notes

Reaction equation

HRID 1514825 reaction equation
[CH3:1][N:2]([C@@H:10]([CH3:38])[C:11](=[O:37])[NH:12][C@@H:13]([CH2:34][C:35]#[CH:36])[C:14](=[O:33])[N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:32])[NH:21][C@H:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)C(=O)OC(C)(C)C.C(OCC)(=O)C.[ClH:45]>O1CCOCC1>[ClH:45].[CH3:1][NH:2][C@@H:10]([CH3:38])[C:11]([NH:12][C@@H:13]([CH2:34][C:35]#[CH:36])[C:14]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([NH:21][C@H:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)=[O:32])=[O:33])=[O:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 59512057HCID 59512057, compound

Product 1

HCID 87173151HCID 87173151, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound of Example 3 (33 mg) was dissolved in 4N HCl in dioxane (2 mL). This was stirred for approximately 15 mins. By TLC (100% ethyl acetate), UV spot was baseline. Excess 4N HCl in dioxane was removed via vacuum. For final compounds, material was left on vacuum pump overnight. For batch 2, material was dissolved in HPLC grade water, filtered through a 0.45 micron filter, and lyophilized overnight to give the title compound as a white semi-fluffy solid. 1H NMR (CD3OH): consistent with proposed structure. MS (m/z): 424.3.

Workup

  1. customExcess 4N HCl in dioxane was removed via vacuum
  2. waitFor final compounds, material was left on vacuum pump overnight
  3. dissolutionFor batch 2, material was dissolved in HPLC grade water
  4. filtrationfiltered through a 0.45 micron
  5. filtrationfilter
  6. waitlyophilized overnight

Sources & evidence

ORD record
ord-69058476c3c74156953f8031da8b0ee4
Source dataset
uspto-grants-2012_07
Patent number
US08222291B2

Reaction notes

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