Acetyl chloride → HCID 178475408, compound

HRID 2248007Notes

Reaction equation

HRID 2248007 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 IN 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 (Na ) 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. customThe organic phase was dried (Na )
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (4:1/ether:hexane)

Sources & evidence

ORD record
ord-d4836a33c49b483dbed39c9227cb2886
Source dataset
uspto-grants-1991_08
Patent number
US05037819

Reaction notes

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