Hydrochloric Acid → Ureidovaline

HRID 52748

Reaction equation

HRID 52748 reaction equation
C[O:2][C:3](=[O:22])[C@H:4]([CH:19]([CH3:21])[CH3:20])[NH:5][C:6]([N:8]([CH3:18])[CH2:9][C:10]1[N:11]=[C:12]([CH:15]([CH3:17])[CH3:16])[S:13][CH:14]=1)=[O:7].O.[OH-].[Li+].C1COCC1.Cl>O>[CH3:18][N:8]([C:6]([NH:5][C@H:4]([C:3]([OH:22])=[O:2])[CH:19]([CH3:20])[CH3:21])=[O:7])[CH2:9][C:10]1[N:11]=[C:12]([CH:15]([CH3:17])[CH3:16])[S:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 10520283N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine Methyl Ester

Product 1

HCID 9818282Ureidovaline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a one liter three neck flask was charged the product of Example 73C (50 g, 0.153 mol), lithium hydroxide monohydrate (13 g, 0.310 mol), 200 ml THF and 190 ml water. This hazy solution was stirred for 2 hours. The reaction was quenched with a solution of conc. HCl (32.4 g, 0.329 mol) in 65 mL water, the THF was removed under vacuum and the product extracted into methylene chlodde (3×210 ml). (NOTE: If necessary, the pH of the aqueous layer should be adjusted to maintain pH 1-4 during the extractions.) The combined organics were then dried with 50 g sodium sulfate, filtered with a 150 ml methylene chloride rinse of the sodium sulfate, and the solvent was removed under vacuum. The product was dissolved in 450 ml THF and again the solvent was removed. Next the product was dissolved in 475 ml THF containing 0.12 g butylated hydroxytoluene (BHT) for storage. If desired, the solvent can be removed under vacuum and the residual syrup dried in a vacuum oven at 55° C. to provide a glassy solid.

Workup

  1. customthe THF was removed under vacuum
  2. extractionthe product extracted into methylene chlodde (3×210 ml)
  3. temperatureto maintain pH 1-4
  4. extractionduring the extractions
  5. dry with material) The combined organics were then dried with 50 g sodium sulfate
  6. filtrationfiltered with a 150 ml methylene chloride
  7. washrinse of the sodium sulfate
  8. customthe solvent was removed under vacuum
  9. dissolutionThe product was dissolved in 450 ml THF
  10. customagain the solvent was removed
  11. dissolutionNext the product was dissolved in 475 ml THF containing 0.12 g butylated hydroxytoluene (BHT) for storage
  12. customthe solvent can be removed under vacuum
  13. customthe residual syrup dried in a vacuum oven at 55° C.
  14. customto provide a glassy solid

Sources & evidence

ORD record
ord-723d644229e944d79df496821d8696d7
Source dataset
uspto-grants-1997_04
Patent number
US05616720

Linked notes

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