Acetyl chloride → HCID 178475408, compound

HRID 1728496Notes

Reaction equation

HRID 1728496 reaction equation
[C:1]([O:4][CH:5]1[NH:8][C:7](=[O:9])[CH:6]1[CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])=[N:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:47](Cl)(=[O:49])[CH3:48]>C1COCC1>[C:1]([O:4][CH:5]1[N:8]([C:47](=[O:49])[CH3:48])[C:7](=[O:9])[CH:6]1[CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])=[N:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178475771HCID 178475771, compound

Product 1

HCID 178475408HCID 178475408, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a -78° C. THF (20 mL) solution of compound 13 (trans:cis ratio, 2:1; 580 mg; 1.16 mmol) was added 1N THF solution of sodium bis(trimethylsilyl)amide (1.36 mL, 1.36 mmol), followed by 10 min stirring of the resultant solution. Acetyl chloride (96 mL, 1.36 mmol) was added, and the temperature of the resultant solution was raised to room temperature, stirred for 30 min, and concentrated. The residue was partitioned between ether and water. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (4:1/ether:hexane) to afford 420 mg (57%) of the product as a mixture of trans and cis (2:1) isomers.

Workup

  1. customTo a -78° C
  2. concentrationconcentrated
  3. customThe residue was partitioned between ether and water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (4:1/ether:hexane)

Sources & evidence

ORD record
ord-85af82bc143f439e993553c265736b21
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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