Hydrochloric Acid → HCID 67019495, compound

HRID 1799413Notes

Reaction equation

HRID 1799413 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, compound2×

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 to 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-17528f1b06874d9dab24534c06bc1498
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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