Potassium Carbonate → HCID 67315890, compound

HRID 1453678Notes

Reaction equation

HRID 1453678 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12](=[O:20])(=[O:19])[N:11]=2)=[CH:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12](=[O:19])(=[O:20])[N:11]=2)=[CH:2]1)([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 79177tert-Butyl bromoacetate2×HCID 67316169HCID 67316169, compound

Product 1

HCID 67315890HCID 67315890, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the product from example 1, step b (300 mg) was dissolved in DMF and treated with K2CO3 (166 mg, 1.2 mmol) followed by t-butyl bromoacetate (150 μL, 1 mmol). The reaction was heated to 80° C. for 1 h. Additional K2CO3 and t-butyl bromoacetate were added (1 mmol each) and the reaction was heated to 100° C. for 2 h. The reaction was cooled and partitioned between EtOAc and water. The organic layer was washed with water 3 times then dried over MgSO4 and concentrated to give the sub-title compound as a yellow solid. MS: ESI (positive): 397 (N4+H).

Workup

  1. temperaturethe reaction was heated to 100° C. for 2 h
  2. temperatureThe reaction was cooled
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed with water 3 times
  5. dry with materialthen dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9757e2a7b1e5432ab639efb36f598cc2
Source dataset
uspto-grants-2009_01
Patent number
US07476667B2

Reaction notes

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