Hydrochloric Acid → HCID 67019495, compound

HRID 1160545Notes

Reaction equation

HRID 1160545 reaction equation
CC(OC([N:8]([CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)[NH:9]C(OC(C)(C)C)=O)=O)(C)C.[ClH:28]>O1CCOCC1>[ClH:28].[CH3:25][O:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:18]([CH2:17][NH:8][NH2:9])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59516112HCID 59516112, compound

Product 1

HCID 67019495HCID 67019495, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-[[(2-methylpropan-2-yl)oxycarbonyl-[(2-methylpropan-2-yl)oxycarbonylamino]amino]methyl]benzoate (Intermediate#54) (3.3 g, 8.67 mmol) in 4M HCl in Dioxane (100 mL) was stirred overnight at ambient temperature. The solvent was removed under reduced pressure and the resulting solid was dissolved in hot MeOH. The hot suspension was filtered then evaporated in vacuo to give a solid. This solid was triturated with ether, filtered then dried under high vac to yield the title compound as a yellow solid (1.5 g, 80%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting solid was dissolved in hot MeOH
  3. filtrationThe hot suspension was filtered
  4. customthen evaporated in vacuo
  5. customto give a solid
  6. customThis solid was triturated with ether
  7. filtrationfiltered
  8. customthen dried under high vac

Sources & evidence

ORD record
ord-1db4a23eec604f78a4ed13d8a10df038
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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