Imidazole → HCID 58604476, compound

HRID 1743256Notes

Reaction equation

HRID 1743256 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH2:16][OH:17])([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@:9]([CH2:16][O:17][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 58604491HCID 58604491, compound

Product 1

HCID 58604476HCID 58604476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.3 g of (S)-2-tert-butoxycarbonylamino-2-hydroxymethylpent-4-enoic acid were dissolved in 10 ml of dimethylformamide. 1.44 g of imidazole and 1.7 g of tert-butyl-dimethylsilyl chloride were added thereto. The mixture was stirred at room temperature for 14 h and then partitioned between 150 ml of water and 200 ml of diethyl ether. The aqueous phase was extracted twice with 100 ml of diethyl ether each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo and the residue was taken up in 20 ml of THF and 60 ml of methanol. 11 ml of a 1 M potassium carbonate solution were added, and the mixture was stirred at room temperature for 2 h. Then 150 ml of a saturated sodium chloride solution were added, and the pH of the solution was adjusted to 2 with 1 M HCL solution. The aqueous phase was extracted 3 times with 100 ml of ethyl acetate each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo, and the crude product was employed without further purification in the next reaction.

Workup

  1. custompartitioned between 150 ml of water and 200 ml of diethyl ether
  2. extractionThe aqueous phase was extracted twice with 100 ml of diethyl ether each time
  3. dry with materialthe combined organic phases were dried with MgSO4
  4. customThe solvents were removed in vacuo
  5. addition11 ml of a 1 M potassium carbonate solution were added
  6. stirringthe mixture was stirred at room temperature for 2 h
  7. additionThen 150 ml of a saturated sodium chloride solution were added
  8. extractionThe aqueous phase was extracted 3 times with 100 ml of ethyl acetate each time
  9. dry with materialthe combined organic phases were dried with MgSO4
  10. customThe solvents were removed in vacuo
  11. customthe crude product was employed without further purification in the next reaction

Sources & evidence

ORD record
ord-b3617c94b5a44de395a3577cc463c9cd
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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