Benzyl 1-(2,3-dihydroxy-3-methyl-1-phenethylbutylcarbamoyl)-3-methylbutylcarbamate → Benzyl 1-(3-hydroxy-3-methyl-2-oxo-1-phenethylbutylcarbamoyl)-3-methylbutylcarbamate

HRID 1634033Notes

Reaction equation

HRID 1634033 reaction equation
[OH:1][CH:2]([C:31]([OH:34])([CH3:33])[CH3:32])[CH:3]([NH:12][C:13]([CH:15]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.I([O-])(=O)(=O)=O>C(Cl)Cl>[OH:34][C:31]([CH3:33])([CH3:32])[C:2](=[O:1])[CH:3]([NH:12][C:13]([CH:15]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 70000370Benzyl 1-(2,3-dihydroxy-3-methyl-1-phenethylbutylcarbamoyl)-3-methylbutylcarbamateHCID 131723735Dess-Martin Periodate

Product 1

HCID 23551313Benzyl 1-(3-hydroxy-3-methyl-2-oxo-1-phenethylbutylcarbamoyl)-3-methylbutylcarbamateYield 20.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution comprised of benzyl 1-(2,3-dihydroxy-3-methyl-1-phenethylbutylcarbamoyl)-3-methylbutylcarbamate (0.250 g, 0.532 mmol) and Dess-Martin Periodate (0.451 g, 1.06 mmol) in dry methylene chloride (27 mL) was stirred vigorously and then a mixture of wet methylene chloride (20 mL, 95 mL of dry methylene chloride and 95 μL of water) was added by a separatory funnel. The mixture was stirred 18 hours at room temperature and concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4) and concentrated to dryness in vacuo. Product was purified from the residue by prep HPLC using 100% water to 20% water/acetonitrile over a 60 minute period. The desired fractions were collected and lyophilized to dryness to provide benzyl 1-(3-hydroxy-3-methyl-2-oxo-1-phenethylbutylcarbamoyl)-3-methylbutylcarbamate (0.05 g, 0.11 mmol) as a white solid. 1H NMR (CDCl3): 0.89-0.91 (m, 6H), δ 1.23-1.32 (2×s, 6H), δ 1.42-4.65 (m, 2H), δ 1.86-1.89 (m, 1H), δ 2.05-2.15 (m, 1H), δ 2.58-2.63 (m, 2H), δ 4.12 (m, 1H), δ 5.09-5.21 (m, 4H), δ 6.52 (d, 1H), δ 7.12-7.31 (m, 10H).

Workup

  1. additionwas added by a separatory funnel
  2. stirringThe mixture was stirred 18 hours at room temperature
  3. concentrationconcentrated to dryness in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to dryness in vacuo
  8. customProduct was purified from the residue by prep HPLC
  9. customover a 60 minute
  10. customThe desired fractions were collected

Sources & evidence

ORD record
ord-922f6d60733540f18bd95ff0e7926f07
Source dataset
uspto-grants-2003_01
Patent number
US06506733B1

Reaction notes

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