Tetrahydrofuran → HCID 66756930, compound

HRID 1643224Notes

Reaction equation

HRID 1643224 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].[CH2:31]1COCC1>>[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][CH2:24][CH3:31])[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 3

HCID 8028TetrahydrofuranHCID 66757176HCID 66757176, compoundHCID 178418339Butyllithium

Product 1

HCID 66756930HCID 66756930, compound

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 TEF (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 chromatography 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 chromatography

Sources & evidence

ORD record
ord-63fb26ea71dd419b8ae603b0401d9c47
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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