Hydrochloric Acid → HCID 89614782, compound

HRID 2177866Notes

Reaction equation

HRID 2177866 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:35])[CH:5]([N:20](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[CH2:6][N:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1>C(OC(C)C)(=O)C>[CH3:2][O:3][C:4](=[O:35])[CH:5]([NH2:20])[CH2:6][N:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[N:9]=[CH:10][CH:11]=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58981196HCID 58981196, compound

Product 1

HCID 89614782HCID 89614782, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

470 ml of 5N hydrochloric acid were added dropwise to a solution of 100 g (212 mmol) of 2-[bis-(tert-butoxycarbonyl)]amino-3-(phenyl-pyrimidin-2-yl-amino)propionic acid methyl ester in 1000 ml of isopropyl acetate at 15° C., and the mixture was stirred for 2 h. Then the phases were separated and the pH of the aqueous phase was adjusted to 8.5 by addition of an aqueous solution of ammonia under cooling in an ice bath. The aqueous phase was extracted with ethyl acetate, and the extract washed with a saturated solution of sodium chloride, dried over sodium sulfate and evaporated in vacuo to give 52.8 g (92%) of 2-amino-3-(phenyl-pyrimidin-2-yl-amino)propionic acid methyl ester as a yellow oil.

Workup

  1. customThen the phases were separated
  2. additionthe pH of the aqueous phase was adjusted to 8.5 by addition of an aqueous solution of ammonia
  3. temperatureunder cooling in an ice bath
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe extract washed with a saturated solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-db0c1b60cd9f43be9f9e024172213c9f
Source dataset
uspto-grants-2015_06
Patent number
US09067918B2

Reaction notes

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