Sodium Bicarbonate → Aliskiren

HRID 500016Notes

Reaction equation

HRID 500016 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:26][C@H:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[CH:33]=1)[CH:28]([CH3:30])[CH3:29])[C@@H:9]([OH:25])[CH2:10][C@H:11]([C:15](=[O:24])[NH:16][CH2:17][C:18]([C:21](=[O:23])[NH2:22])([CH3:20])[CH3:19])[CH:12]([CH3:14])[CH3:13])(C)(C)C.C(=O)(O)[O-].[Na+]>Cl.O1CCOCC1>[NH2:7][C@@H:8]([CH2:26][C@H:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[CH:33]=1)[CH:28]([CH3:29])[CH3:30])[C@@H:9]([OH:25])[CH2:10][C@@H:11]([CH:12]([CH3:13])[CH3:14])[C:15]([NH:16][CH2:17][C:18]([C:21](=[O:23])[NH2:22])([CH3:20])[CH3:19])=[O:24]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 53348234tert-Butyl [(3S,5S,6S,8S)-8-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-6-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-2,9-dimethyldecan-5-yl]carbamate

Product 1

HCID 5493444Aliskiren

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Product 13 is dissolved in a mixture of 4.0M hydrochloric acid in dioxane. The solution is stirred for 24 hours at room temperature and neutralized with solid sodium bicarbonate. The suspension is filtered and the solvent removed in vacuum to give the product as a foam (for characterization see e.g. EP 0 678 503, Example 137).

Workup

  1. filtrationThe suspension is filtered
  2. customthe solvent removed in vacuum

Sources & evidence

ORD record
ord-ab4596c6eae7472bb5bd1d8be44d3a6c
Source dataset
uspto-grants-2010_08
Patent number
US07767831B2

Reaction notes

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