Potassium Carbonate → HCID 70298449, compound

HRID 1106904Notes

Reaction equation

HRID 1106904 reaction equation
C1O[C:3]([CH2:10][C:11]([N:13]([CH:15]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=2)[CH2:16][N:17]2[CH2:21][CH2:20][CH:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:18]2)[CH3:14])=[O:12])=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[C:37](=O)([O-])[O-:38].[K+].[K+].[C:43]([O:47][C:48](=[O:51])[CH2:49]Br)([CH3:46])([CH3:45])[CH3:44]>CN(C=O)C.O>[C:43]([O:47][C:48](=[O:51])[CH2:49][O:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([CH:15]([N:13]([C:11](=[O:12])[CH2:10][C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:38][CH:37]=2)[CH3:14])[CH2:16][N:17]2[CH2:21][CH2:20][CH:19]([O:22][Si:23]([C:26]([CH3:28])([CH3:27])[CH3:29])([CH3:24])[CH3:25])[CH2:18]2)[CH:31]=1)([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 70298102HCID 70298102, compound

Product 1

HCID 70298449HCID 70298449, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 25 (2.195 g, 4.32 mmol) in DMF (40 mL) was added powdered potassium carbonate (1.21 g, 8.77 mmol) followed by t-butylbromoacetate (0.85 mmol, 5.26 mmol). After stirring for 18 hours, the solution was diluted with water (100 mL) and extracted with ethyl acetate (4×150 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. Purification by column chromatography in ethyl acetate:heptane (6:4) gave the product as an oil. Yield=1.209 g, 45%.

Workup

  1. extractionextracted with ethyl acetate (4×150 mL)
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography in ethyl acetate:heptane (6:4)

Sources & evidence

ORD record
ord-a9eb623811ee455a8ee34917d939d360
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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