Hydrochloric Acid → tert-butyl (1S)-1-[(2S)-4-(4-bromobenzyl)-5-oxotetrahydro-2-furanyl]-2-phenylethylcarbamate

HRID 1174262Notes

Reaction equation

HRID 1174262 reaction equation
[Br:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][C:7]2(C(OCC)=O)[CH2:11][C@@H:10]([C@@H:12]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:9][C:8]2=[O:28])=[CH:4][CH:3]=1.Cl>C(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:8](=[O:28])[O:9][C@H:10]([C@@H:12]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11]2)=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67406735ethyl (5S)-3-(4-bromobenzyl)-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-2-oxotetrahydro-3-furancarboxylate

Product 1

HCID 86598818tert-butyl (1S)-1-[(2S)-4-(4-bromobenzyl)-5-oxotetrahydro-2-furanyl]-2-phenylethylcarbamateYield 94.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product from Example 92A (22.4 g) in ethanol (120 mL) was treated with LiOH monohydrate (8.0 g, 190.7 mmol) solution in water (30 mL) and the mixture was stirred at 25° C. for 16 hours. The mixture was cooled to 0° C., adjusted to pH 5 by addition of 4N HCl and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the concentrate in toluene (400 mL) was then heated at reflux for 18 hours, cooled and concentrated to give the title compound (18.4 g), which was used without further purification.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. custompartitioned between dichloromethane and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationA solution of the concentrate in toluene (400 mL)
  8. temperaturewas then heated
  9. temperatureat reflux for 18 hours
  10. temperaturecooled
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-bca720b1212c459aba21c7687ab1d6f9
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…