HCID 66757176, compound → HCID 69513733, compound

HRID 457391Notes

Reaction equation

HRID 457391 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[CH2:6]([N:10]1[C:14]([CH:15]=[N:16][N:17]2[CH2:21][CH2:20][CH2:19][C@@H:18]2[CH2:22][O:23][CH3:24])=[CH:13][N:12]=[C:11]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:7][CH2:8][CH3:9]>C1COCC1>[CH2:6]([N:10]1[C:14]([C@@H:15]([NH:16][N:17]2[CH2:21][CH2:20][CH2:19][C@@H:18]2[CH2:22][O:23][CH3:24])[CH2:2][CH2:3][CH2:4][CH3:5])=[CH:13][N:12]=[C:11]1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 66757176HCID 66757176, compoundHCID 178418339Butyllithium

Product 1

HCID 69513733HCID 69513733, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of BuLi (2.5 M in hexane, 12.5 ml, 31 mmol) under argon in anhydrous THF (15 mL) at −78° C. is slowly added a solution of crude 192 (14 mmol) in THF (15 mL). The mixture is allowed to warm to room temperature over a period of 15 h and quenched with saturated sodium bicarbonate. The aqueous phase is extracted with ethyl acetate and the combined organic phases were washed with water and dried over sodium sulfate. Removal of solvents under reduced pressure and purification of the residue by column chromatograpy affords the desired product as a colorless syrup. Yield: 5.1 g; [α]D−72 (c=1.2, CHCl3); LC-MS (MH+): 399.

Workup

  1. customquenched with saturated sodium bicarbonate
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washthe combined organic phases were washed with water
  4. dry with materialdried over sodium sulfate
  5. customRemoval of solvents
  6. customunder reduced pressure and purification of the residue by column chromatograpy

Sources & evidence

ORD record
ord-2b022679edb141f6878d6ec6d83db737
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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