Dichloromethane → Ramipril

HRID 2187112

Reaction equation

HRID 2187112 reaction equation
C(O)(=O)/C=C\C(O)=O.C([O:16][C:17]([C@H:19]1[N:23]([C:24](=[O:42])[C@@H:25]([NH:27][C@H:28]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:26])[C@H:22]2[CH2:43][CH2:44][CH2:45][C@H:21]2[CH2:20]1)=[O:18])C1C=CC=CC=1.ClCCl>C(N(CC)CC)C>[CH3:41][CH2:40][O:39][C:37]([C@@H:28]([NH:27][C@H:25]([C:24]([N:23]1[C@H:19]([C:17]([OH:18])=[O:16])[CH2:20][C@H:21]2[C@@H:22]1[CH2:43][CH2:44][CH2:45]2)=[O:42])[CH3:26])[CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:38]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 10121882(2s,3As,6as)-1-[(s)-2-[[(s)-1-(ethoxycarbonyl)-3-phenylpropyl]-amino]propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid benzyl ester maleic acid salt

Product 1

HCID 5362129Ramipril

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
2.5 °C

Procedure

A 1.0 g portion of (2S,3aS,6aS)-1-[(S)-2-[[(S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid benzyl ester maleic acid salt 1 was placed into 100 mL of dichloromethane, and was cooled to 0-5° C. Triethylamine (0.19 g) was added to the mixture. The resulting mixture was washed with water, and the organic phase was evaporated to give an oil. This oil was deprotected using hydrogenolysis, as per examples stated in EP 079022 to give Ramipril as a white solid.

Workup

  1. washThe resulting mixture was washed with water
  2. customthe organic phase was evaporated
  3. customto give an oil

Sources & evidence

ORD record
ord-2ba52ce1ab474547a63de27377c6daf5
Source dataset
uspto-grants-2002_06
Patent number
US06407262B1

Linked notes

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