Hydrochloric Acid → HCID 15372706, compound

HRID 394680Notes

Reaction equation

HRID 394680 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]1([C:14]2[O:15][C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[O:18][C:19]=2[CH2:20][NH2:21])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.CCOC(C)=O>N1C=CC=CC=1.ClCCl>[C:8]1([C:14]2[O:15][C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[O:18][C:19]=2[CH2:20][NH:21][C:1](=[O:3])[CH3:2])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 15372703HCID 15372703, compound

Product 1

HCID 15372706HCID 15372706, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.416 ml (4.4 mmol) of acetic anhydride are slowly added to a solution of 0.88 g (3.67 mmol) of the amine obtained in Step C in 10 ml of anhydrous pyridine previously cooled to 0° C. After 1 hour of stirring under argon, the medium is diluted with dichloromethane and then acidified with a hydrochloric acid solution (1N). The aqueous phase is then extracted with dichloromethane; the organic phases are then dried over magnesium sulphate. The solvent is evaporated in vacuo; the residue obtained is then passed over a silica column (eluant: AcOEt/PE: 60/40) to yield the title amide in the form of a white solid.

Workup

  1. extractionThe aqueous phase is then extracted with dichloromethane
  2. dry with materialthe organic phases are then dried over magnesium sulphate
  3. customThe solvent is evaporated in vacuo
  4. customthe residue obtained

Sources & evidence

ORD record
ord-41d453d877c44d14810cdc9a8596ff4f
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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