Triethylamine → Perindopril Benzyl Ester

HRID 900394Notes

Reaction equation

HRID 900394 reaction equation
[NH2:1][C@@H:2]([CH2:8][CH2:9][CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.Br[C@H:19]([CH3:41])[C:20]([N:22]1[C@@H:30]2[C@@H:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24][C@H:23]1[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])=[O:21]>C(#N)C>[CH2:6]([O:5][C:3]([C@@H:2]([NH:1][C@@H:19]([CH3:41])[C:20]([N:22]1[C@@H:30]2[C@@H:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24][C@H:23]1[C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])=[O:21])[CH2:8][CH2:9][CH3:10])=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10080526ethyl (2S)-2-aminopentanoateHCID 11315392benzyl (2S,3aS,7aS)-1-[(2R)-2-bromopropionyl]octahydro-1H-indole-2-carboxylate

Product 1

HCID 11396975Perindopril Benzyl Ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Introduce 123 g of ethyl (2S)-2-aminopentanoate, 160 ml of triethylamine and 160 ml of acetonitrile into a reactor, and then bring the mixture to 60° C., slowly add the solution obtained in Step A and reflux for 4 hours. After returning to ambient temperature, wash the mixture with water and with a dilute acetic acid solution, and then evaporate off the solvents to yield benzyl (2S,3aS,7aS)-1-{(2S)-2-[(1S)-1-(ethoxycarbonyl)butylamino]-propionyl}octahydro-1H-indole-2-carboxylate.

Workup

  1. customto 60° C.
  2. temperaturereflux for 4 hours
  3. customAfter returning to ambient temperature
  4. washwash the mixture with water
  5. customwith a dilute acetic acid solution, and then evaporate off the solvents

Sources & evidence

ORD record
ord-16be0b7180d344538a908adc42d47ff8
Source dataset
uspto-grants-2008_04
Patent number
US07358372B2

Reaction notes

Loading…