Water → 2-Trimethylsilanylethyl (r)-4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-4-oxobutyl)piperidine-1-carboxylate

HRID 1743270Notes

Reaction equation

HRID 1743270 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]([C:29]([O:31][CH3:32])=[O:30])([CH2:26][CH:27]=C)[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:34].[Na+].O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@:9]([C:29]([O:31][CH3:32])=[O:30])([CH2:26][CH:27]=[O:34])[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH2:21][Si:22]([CH3:23])([CH3:25])[CH3:24])=[O:18])[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 909187592-Trimethylsilanylethyl (s)-4-(2-tert-butoxycarbonylamino-2-methoxycarbonylpent-4-enyl)piperidine-1-carboxylate

Product 1

HCID 915778092-Trimethylsilanylethyl (r)-4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-4-oxobutyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

750 mg of 2-trimethylsilanylethyl (S)-4-(2-tert-butoxycarbonylamino-2-methoxycarbonylpent-4-enyl)piperidine-1-carboxylate were dissolved in 30 ml of THF. 852 mg of sodium periodate and 10 ml of water were added. The mixture was then stirred at room temperature for 3 h and filtered through kieselguhr. The filter cake was washed twice with 10 ml of THF each time. The THF was removed in vacuo, and the residue was partitioned between 30 ml of water and 30 ml of ethyl acetate. The pH of the aqueous phase was adjusted to 2 with 1 N HCl solution. The phase were separated and the aqueous phase was extracted twice with 20 ml of ethyl acetate each time. The combined organic phases were dried with MgSO4. The solvents were removed in vacuo and the residue was chromatographed on silica gel.

Workup

  1. filtrationfiltered through kieselguhr
  2. washThe filter cake was washed twice with 10 ml of THF each time
  3. customThe THF was removed in vacuo
  4. customthe residue was partitioned between 30 ml of water and 30 ml of ethyl acetate
  5. customThe phase were separated
  6. extractionthe aqueous phase was extracted twice with 20 ml of ethyl acetate each time
  7. dry with materialThe combined organic phases were dried with MgSO4
  8. customThe solvents were removed in vacuo
  9. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-fd5d4b48fd8043508b439c016576f652
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

Loading…