Hydrochloric Acid → HCID 69933682, compound

HRID 2416642Notes

Reaction equation

HRID 2416642 reaction equation
C(OC([NH:8][C@@H:9]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)[C:10]([NH:12][CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)=[O:15])=[O:11])=O)(C)(C)C.Cl>CO.C(OCC)(=O)C>[NH2:8][C@@H:9]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)[C:10]([NH:12][CH2:13][C:14]([N:16]1[CH2:17][CH2:18][N:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:20][CH2:21]1)=[O:15])=[O:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69934617HCID 69934617, compound

Product 1

HCID 69933682HCID 69933682, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (2S)-2-(tert-butoxycarbonylamino)-N-[2-[4-(4-chlorophenyl)-1-piperazinyl]-2-oxoethyl]-3-(2-pyridyl)-propanamide (42 g) in methanol (84 ml) was added 4N hydrogen chloride in ethyl acetate (209 ml) at 0° C. and the mixture was stirred at 0° C. for 30 minutes. The reaction mixture was allowed to warm to room temperature, stirred for 2 hours and diluted with ethyl acetate. The resulting solid was collected by filtration and washed with ethyl acetate. The solid was poured into aqueous sodium hydrogencarbonate solution and the mixture was extracted with chloroform. The aqueous layer was extracted twice with chloroform. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give a crude product of the title compound (27 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with ethyl acetate
  5. additionThe solid was poured into aqueous sodium hydrogencarbonate solution
  6. extractionthe mixture was extracted with chloroform
  7. extractionThe aqueous layer was extracted twice with chloroform
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e162950a5b374175a76a260c1a85880a
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

Loading…