Hydrogen Peroxide → HCID 22861550, compound

HRID 1737114Notes

Reaction equation

HRID 1737114 reaction equation
C([O:8][C:9](=[O:38])[CH:10]([CH2:13][C:14]1[N:15]=[CH:16][N:17]([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=1)[CH2:11][CH3:12])C1C=CC=CC=1.OO.[OH2:41].[OH-:42].[Li+]>C1COCC1.O>[C:26]1([C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:17]2[CH:18]=[C:14]([CH2:13][C@H:10]([CH2:11][C:12]([OH:42])=[O:41])[C:9]([OH:8])=[O:38])[N:15]=[CH:16]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 86749668HCID 86749668, compound

Product 1

HCID 22861550HCID 22861550, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

4-{[1(S)-(Cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino}-4-oxo-3(R)-{[(1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}butanoic acid benzyl ester: A 30% aqueous solution of H2O2 (4.70 mL, 41.6 mmol) and lithium hydroxide monohydrate (436 mg, 10.4 mmol) were added serially to cooled solution (0°) of the product of section (c) of this example (6.67 g, 10.4 mmol) in THF-H2O (156 mL: 52 mL). The reaction mixture was stirred at 0° for 2 h and then at room temperature for 2 h. Excess peroxide was quenched at 0° with 1.5N aqueous Na2SO3 solution. THF was removed by distillation under reduced pressure. The concentrate was poured into H2O (500 mL). The mixture was rendered acid by the addition of a 10% (w/v) aqueous solution of citric acid, and then extracted with EtOAc. The extract was washed with brine, dried (MgSO4) and evaporated to dryness under reduced pressure to yield the desired monoprotected dicarboxylic acid, i.e. the 4-(phenylmethyl) ester of 2(R)-{[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl}butanedioic acid. The monoprotected dicarboxylic acid was used for the following coupling step without further purification.

Workup

  1. waitat room temperature for 2 h
  2. customExcess peroxide was quenched at 0° with 1.5N aqueous Na2SO3 solution
  3. customTHF was removed by distillation under reduced pressure
  4. additionThe concentrate was poured into H2O (500 mL)
  5. additionby the addition of a 10% (w/v) aqueous solution of citric acid
  6. extractionextracted with EtOAc
  7. washThe extract was washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-41c59cf897884792b0e283ae2a0fb102
Source dataset
uspto-grants-1996_07
Patent number
US05541163

Reaction notes

Loading…