Acrylamide → HCID 86660582, compound

HRID 1499375Notes

Reaction equation

HRID 1499375 reaction equation
[CH:1](=[N:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:10]([O:12]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([NH2:33])(=[O:32])[CH:30]=[CH2:31].CC(C)([O-])C.[K+]>C1COCC1>[CH:1](=[N:8][C:9]1([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:20])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:31][CH2:30][C:29](=[O:32])[NH:33][C:10]1=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6579AcrylamideHCID 23665647Potassium tert-butoxideHCID 67997651HCID 67997651, compound

Product 1

HCID 86660582HCID 86660582, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2 (4 g, 10.4 mmol) and acrylamide (1.11 g, 15.7 mmol) in THF (40 mL) was added portionwise potassium tert-butoxide (1.23 g, 11.0 mmol) over a period of 15 min at 0° C. After 3.5 h, the mixture was quenched with aqueous NH4Cl and extracted into EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated to afford 3 (3.6 g, 82%) without further purification. Rf=0.33 (95:5 DCM:MeOH).

Workup

  1. customthe mixture was quenched with aqueous NH4Cl
  2. extractionextracted into EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a0895881b5b49418541eb754f2febc6
Source dataset
uspto-grants-2015_12
Patent number
US09200263B2

Reaction notes

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