Hydrochloric Acid → HCID 131729841, compound

HRID 1515540Notes

Reaction equation

HRID 1515540 reaction equation
[CH:1]([S:4]([C:7]1[C:8]([C@H:13]2[C@@H:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:15][N:14]2C(OC(C)(C)C)=O)=[N:9][CH:10]=[CH:11][CH:12]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[ClH:30].O1CCOCC1>CCOC(C)=O>[ClH:30].[CH:1]([S:4]([C:7]1[C:8]([C@H:13]2[C@@H:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:15][NH:14]2)=[N:9][CH:10]=[CH:11][CH:12]=1)(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59479418HCID 59479418, compound

Product 1

HCID 131729841HCID 131729841, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 65J (0.38 g, 0.89 mmol) in EtOAc (5 mL) at rt was added 4.0 N HCl in dioxane (5 mL, 20 mmol). The mixture was stirred at rt for 8.0 h. After removal of the solvent, the crude was diluted in methylene chloride and washed with sat. NaHCO3. The aqueous was extracted with methylene chloride (3×80 mL). The combined organic layer was dried over Na2SO4. After removal of solvent 65K (0.28 g, 95% yield) was obtained as viscous oil. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.15 (t, J=7.03 Hz, 3H) 1.23-1.27 (d, J=7.03 Hz, 3H) 1.30 (d, J=7.03 Hz, 3H) 2.21-2.27 (m, 2H) 3.07 (ddd, J=11.10, 7.47, 7.36 Hz, 1H) 3.41 (ddd, J=9.34, 7.25, 7.14 Hz, 1H) 3.54-3.63 (m, 1H) 4.03-4.12 (m, 2H) 5.14 (d, J=7.03 Hz, 1H) 7.58 (dd, J=7.91, 4.83 Hz, 1H) 8.32 (dd, J=8.35, 1.76 Hz, 1H) 8.86-8.91 (m, 1H), LC-MS 327 (M+H).

Workup

  1. customAfter removal of the solvent
  2. additionthe crude was diluted in methylene chloride
  3. washwashed with sat. NaHCO3
  4. extractionThe aqueous was extracted with methylene chloride (3×80 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-4ed046996b5f4428875d2cbf4f17b80a
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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