Potassium Carbonate → HCID 15392244, compound

HRID 362532Notes

Reaction equation

HRID 362532 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][C:36]([C:42]#[N:43])=[CH:37][CH:38]=4)[CH:33]=3)[S:22]([NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29])(=[O:24])=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:45][C:46]([O:48][CH3:49])=[O:47].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][C:36]([C:42]#[N:43])=[CH:37][CH:38]=4)[CH:33]=3)[S:22]([N:25]([C:26]([O:27][CH2:28][CH3:29])=[O:30])[CH2:45][C:46]([O:48][CH3:49])=[O:47])(=[O:23])=[O:24])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 15392232HCID 15392232, compound

Product 1

HCID 15392244HCID 15392244, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl N-[N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]carbamate (1 g) was dissolved in 10 ml of dimethylformamide, 376 mg of methyl bromoacetate and 339 mg of potassium carbonate were added to the solution, and the mixture was stirred at room temperature for 15 hours. The reaction solution was evaporated, water was added, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography using hexane:ethyl acetate (8:2) as the eluent to give 1.097 g of methyl N-[N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]sulfamoyl]-N-ethoxycarbonylglycinate.

Workup

  1. customThe reaction solution was evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4dc61ad7344b413c985cdd74223a7d5f
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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