Potassium tertbutoxide → HCID 53419638, compound

HRID 1629849Notes

Reaction equation

HRID 1629849 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[O:19][CH3:20])=[O:7].[K].CC(C)([O-])C>CN(C=O)C>[CH3:20][O:19][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:9]=1[N:8]1[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1=[O:7])[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 50987170Potassium tertbutoxideHCID 67048137Methyl 4-(5-chloro-pentanoyl-amino)-3-methoxy-benzoate

Product 1

HCID 53419638HCID 53419638, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2.25 g (7.51 mmol) methyl 4-(5-chloro-pentanoyl-amino)-3-methoxy-benzoate dissolved in 60 ml DMF are combined with 1.26 g (11.2 mmol) potassium-tert.-butoxide and stirred for 2.5 hours at 60° C. Then the mixture is evaporated down i. vac., the residue is combined with water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate, evaporated down i. vac. and the residue obtained is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate 3:2->0:1).

Workup

  1. customThen the mixture is evaporated down i
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customevaporated down i
  5. customand the residue obtained
  6. customis purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate 3:2->0:1)

Sources & evidence

ORD record
ord-7244c4d6c2fe42aa978158b50b3ea481
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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