Hydrogen Peroxide → (1R)-N-benzyloxycarbonyl-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine

HRID 1741391Notes

Reaction equation

HRID 1741391 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]([NH:22][C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH:20]=[CH2:21])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C12BC(CCC1)CCC2.[OH-:42].[Na+].OO>C1COCC1>[CH2:26]([O:25][C:23]([NH:22][C@@H:18]([C:9]1[O:10][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)[CH2:19][CH2:20][CH2:21][OH:42])=[O:24])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 54377108(4R)-4-(4,5-diphenyloxazol-2-yl)-4-benzyloxycarbonylamino-1-butene

Product 1

HCID 53739918(1R)-N-benzyloxycarbonyl-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4R)-4-(4,5-diphenyloxazol-2-yl)-4-benzyloxycarbonylamino-1-butene (5.2 g) in THF (50 ml) was added 9-borabicyclo[3.3.1]nonane (9-BBN) (98 ml, 0.5M solution of THF) at 0° C. After stirred for 4 hours at room temperature, 2N NaOH solution (20 ml) and 35% H2O2 solution (20 ml) were added to the mixture at the 0° C. The mixture was stirred for 1 hour at the same temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (1R)-N-benzyloxycarbonyl-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine (13 g). MS (m/z): 443 (M+ +1) IR (Neat): 3300, 1700 cm-1NMR (CDCl3, δ): 1.6-2.2 (4H, m), 3.68 (2H, m), 5.10-5.2 (1H, m), 5.14 (2H, s), 5.73 (1H, d, J=10.0 Hz), 7.2-7.7 (15H, m)

Workup

  1. stirringThe mixture was stirred for 1 hour at the same temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine
  4. customThe dried solvent was evaporated in vacuo
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7eae3b5c35e74afd8645c0f4b521a64d
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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