Benzoyl chloride → HCID 178475409, compound

HRID 1728500Notes

Reaction equation

HRID 1728500 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:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C1COCC1>[C:1]([O:4][CH:5]1[N:8]([C:47]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:54])[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 7412Benzoyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178475771HCID 178475771, compound

Product 1

HCID 178475409HCID 178475409, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a -78° C. THF (4 mL) of compound 13 (500 mg, 1 mmol) was added 1N THF solution of sodium bis(trimethylsilyl)amide (1.0 mL, 1.0 mmol), and the resultant reaction mixture was stirred for 15 min. Benzoyl chloride (140 mg, 1 mmol) was added, and the mixture was stirred for 30 min at -78° C. and for 90 min at room temperature. The solution was subsequently partitioned between ether and aqueous pH 4.0 buffer. The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (Et2O:hexane/2:1) to afford 200 mg (33%) of the title product as a mixture of trans and cis (3:1) isomers.

Workup

  1. customTo a -78° C
  2. customthe resultant reaction mixture
  3. stirringthe mixture was stirred for 30 min at -78° C. and for 90 min at room temperature
  4. customThe solution was subsequently partitioned between ether and aqueous pH 4.0 buffer
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (Et2O:hexane/2:1)

Sources & evidence

ORD record
ord-4d313be8e6f245cca294a5c463383b3f
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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