Hydrochloric Acid → HCID 11058732, compound

HRID 1870259Notes

Reaction equation

HRID 1870259 reaction equation
C[C@@H]([O:8][C:9]([CH2:11][C@@H:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]([C:23](=[O:36])[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:26][C:25]=2[Cl:35])[CH2:15][CH2:14][CH2:13]1)=[O:10])CCCCC.[OH-].[Na+].Cl>CO>[C:9]([CH2:11][C@@H:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]([C:23](=[O:36])[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:26][C:25]=2[Cl:35])[CH2:15][CH2:14][CH2:13]1)([OH:10])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 10973260HCID 10973260, compound

Product 1

HCID 11058732HCID 11058732, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of (5R)-5-((R)-2-heptyloxycarbonylmethyl)-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (33 g) in methanol (500 ml) is added a 5N aqueous sodium hydroxide solution (25.8 ml), and the mixture is heated with stirring at 40-50° C. for two hours. To the mixture is further added a 5N aqueous sodium hydroxide solution (15 ml), and the mixture is heated with stirring at 50° C. for three hours. The reaction solution is acidified with hydrochloric acid, and concentrated under reduced pressure to remove the methanol, and extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to remove the ethyl acetate. The resultant is crystallized from ethyl acetate--diethyl ether, washed with diethyl ether--n-hexane to give (5R)-5-carboxymethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (21.1 g).

Workup

  1. temperaturethe mixture is heated
  2. temperaturethe mixture is heated
  3. stirringwith stirring at 50° C. for three hours
  4. concentrationconcentrated under reduced pressure
  5. customto remove the methanol
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer is washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto remove the ethyl acetate
  11. customThe resultant is crystallized from ethyl acetate
  12. washdiethyl ether, washed with diethyl ether

Sources & evidence

ORD record
ord-290e5f27099b44e2b7aa60126adeee46
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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