Dichloromethane → HCID 69357284, compound

HRID 852644Notes

Reaction equation

HRID 852644 reaction equation
[C:1]([O:5][C:6](=[O:21])[C:7]1[CH:12]=[C:11]([N:13]2[CH2:17]C[CH2:15][C:14]2=[O:18])[CH:10]=[C:9](NC)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:22][CH2:23][N:24](CC)CC.C(O[C:33](=[O:35])[CH3:34])(=O)C.[CH2:36](Cl)Cl>>[C:1]([O:5][C:6](=[O:21])[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([N:13]([C:14](=[O:18])[CH3:15])[CH3:17])[C:12]=1[N:24]([CH2:23][CH3:22])[C:33](=[O:35])[CH2:34][CH3:36])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 69358506HCID 69358506, compound

Product 1

HCID 69357284HCID 69357284, compoundYield 89%

Procedure

To a solution of 3-methylamino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid tert-butyl ester (B32) (200 mg, 0.69 mmol, 1 equiv) in CH2Cl2 (5 ml) was added NEt3 (278 μl, 2 mmol, 2.9 equiv) and acetic anhydride (195 μl, 2 mmol, 2.9 equiv). The resulting mixture was stirred at room temperature for 16 h, diluted with CH2Cl2, washed with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo to give (acetyl-methyl-amino)-(ethyl-propionyl-amino)-benzoic acid tert-butyl ester (B47) (203 mg, 89%) as a pale yellow oil which was used in the next step without further purification. [M+H]+=333.1 RT=2.76 min

Workup

  1. washwashed with saturated aqueous NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c93589cd48c84c698b2b1ba84f30e47f
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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