Acetyl chloride → HCID 178477454, compound

HRID 1728483Notes

Reaction equation

HRID 1728483 reaction equation
[CH2:1]([S:3][C@@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[CH2:9][CH2:10][CH2:11][NH:12][C:13]([NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[N:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:46](Cl)(=[O:48])[CH3:47]>C1COCC1>[CH2:1]([S:3][C@@H:4]1[N:7]([C:46](=[O:48])[CH3:47])[C:6](=[O:8])[C@H:5]1[CH2:9][CH2:10][CH2:11][NH:12][C:13]([NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[N:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 178477456HCID 178477456, compound

Product 1

HCID 178477454HCID 178477454, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a -78° C. THF (10 mL) solution of compound 17 (718 mg, 1.26 mmol) was added 1N THF solution (1.5 mL) of lithium bis(trimethylsilyl)amide (1.5 mmol), followed by stirring the solution for 10 min. Acetyl chloride (0.1 mL, 1.5 mmol) was added, and the resultant solution was warmed to room temperature, followed by an additional hour of stirring. The reaction mixture was concentrated, and the residue was partitioned between pH 7.0 aqueous buffer and ethyl acetate. The organic phase was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (1:1/Et2O:hexane) to afford 615 mg (90%) of the title product.

Workup

  1. customTo a -78° C
  2. waitfollowed by an additional hour
  3. stirringof stirring
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was partitioned between pH 7.0 aqueous buffer
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (1:1/Et2O:hexane)

Sources & evidence

ORD record
ord-a18e519d8d5c4d79b7c17d5c4d0a0cb3
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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