Hydrochloric Acid → Delapril Hydrochloride

HRID 621178Notes

Reaction equation

HRID 621178 reaction equation
C(OCC)(=O)C.C(=O)([O-])O.[Na+].Br.[CH2:13]([O:15][C:16]([C@@H:18]([NH:27][C@H:28]([C:30]([N:32]([CH:37]1[CH2:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38]1)[CH2:33][C:34]([OH:36])=[O:35])=[O:31])[CH3:29])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH3:14].[ClH:46]>O>[ClH:46].[CH2:13]([O:15][C:16]([C@@H:18]([NH:27][C@H:28]([C:30]([N:32]([CH:37]1[CH2:38][C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:45]1)[CH2:33][C:34]([OH:36])=[O:35])=[O:31])[CH3:29])[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:17])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 13132312HCID 13132312, compound

Product 1

HCID 5362115Delapril Hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 500 ml of ethyl acetate, 33 g of sodium hydrogen carbonate and 500 ml of water is added 16.2 g of N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-N-(indan-2-yl)glycine hydrobromide prepared by the procedure of Example 4. After stirring to complete dissolution, the solution was adjusted to pH 4 with 1N hydrochloric acid. The ethyl acetate layer is separated, washed with water, dried and, after addition of 20 ml of 7N ethanolic hydrochloric acid, concentrated under reduced pressure. To the residue are added 250 ml of ethyl ether and 250 ml of petroleum ether, and the resulting precipitate is collected by filtration to give 11 g of N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-N-(indan-2-yl)glycine hydrochloride as colorless crystals.

Workup

  1. customprepared by the procedure of Example 4
  2. customThe ethyl acetate layer is separated
  3. washwashed with water
  4. customdried
  5. additionafter addition of 20 ml of 7N ethanolic hydrochloric acid
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue are added 250 ml of ethyl ether and 250 ml of petroleum ether
  8. filtrationthe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-9bf2ec3485384dff95cf59aa6da92009
Source dataset
uspto-grants-1989_04
Patent number
US04822818

Reaction notes

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