Hydrochloric Acid → Ureidovaline

HRID 55738

반응식

HRID 55738 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 9818282Ureidovaline

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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 chloride (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.

후처리

  1. customthe THF was removed under vacuum
  2. extractionthe product extracted into methylene chloride (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

출처 및 근거

ORD 기록
ord-096629b79e1241668f53ef78e62dd206
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05625072

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