Acetyl chloride → HCID 18655452, compound

HRID 1707877Notes

Reaction equation

HRID 1707877 reaction equation
[CH:1]1([CH2:4][CH2:5][C:6]([N:8]2[C@@H:12]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][O:10][C:9]2=[O:20])=[O:7])[CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].[C:29](Cl)(=[O:31])[CH3:30]>C1COCC1>[CH:1]1([CH2:4][C@H:5]([C:29](=[O:31])[CH3:30])[C:6]([N:8]2[C@@H:12]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][O:10][C:9]2=[O:20])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 2724682Lithium diisopropylamideHCID 57264739HCID 57264739, compound

Product 1

HCID 18655452HCID 18655452, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under a nitrogen atmosphere, a solution of the (4S)-3-(3-cyclopropyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone (6.01 g, 22.0 mmol, described in example 3) in anhydrous THF (10 mL) was added to a cold (-78°) stirred solution of lithium diisopropylamide (963 mg, 9.0 mmol) in anhydrous THF (10 mL). The mixture was stirred at -78° for 45 min and then transferred by cannula into a cold (-78°) solution of acetyl chloride (0.86 mL, 12 mmol) in anhydrous THF (5 mL). The resultant mixture was stirred for 15 min at -78° C., then quenched with a saturated aqueous solution of NH4Cl, allowed to warm to room temperature (20°-22°) and diluted with Et2O. The layers were separated and the aqueous phase was extracted with Et2O.

Workup

  1. customquenched with a saturated aqueous solution of NH4Cl
  2. additiondiluted with Et2O
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with Et2O

Sources & evidence

ORD record
ord-74826aeabfcf45a4b91288f15ea14015
Source dataset
uspto-grants-1994_10
Patent number
US05354767

Reaction notes

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