Hydrochloric Acid → Delapril Hydrochloride

HRID 1762303Notes

Reaction equation

HRID 1762303 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:20]([CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1)[CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].O1CCOCC1.[ClH:44]>C(OCC)C>[ClH:44].[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:20]([CH:29]1[CH2:30][C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:37]1)[CH2:21][C:22]([OH:24])=[O:23])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 13135303HCID 13135303, compound

Product 1

HCID 5362115Delapril HydrochlorideYield 84.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To tert-butyl N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanyl-N-(2-indanyl)glycinate (1.4 g, 2.75 mmoles) was added p-dioxane which had been saturated with anhydrous hydrogen chloride (35 ml). the resulting solution was stirred for two and a half hourst at room temperature and then solvent was evaporated to afford a colorless solid. Anhydrous diethyl ether was added to the residue and the product was filtered and washed with a small amount of ether to give N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanyl-N-(2-indanyl)glycine hydrochloride (1.1 g, 84.6%) as a colorless solid: m.p. 181°; [α]DETOH=+16.44°; mass spectra (CI): 435.6(m+1-H2O, 100%).

Workup

  1. customa half hourst at room temperature and then solvent was evaporated
  2. customto afford a colorless solid
  3. filtrationthe product was filtered
  4. washwashed with a small amount of ether

Sources & evidence

ORD record
ord-368b075109714272a3aa21d95c8755be
Source dataset
uspto-grants-1989_05
Patent number
US04831184

Reaction notes

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