Sodium Chloride → HCID 87539627, compound

HRID 2242531Notes

Reaction equation

HRID 2242531 reaction equation
[C:1]([C@@H:4]1[CH2:12][C@H:11]2[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[NH:5]1)([OH:3])=[O:2].[C:13]([C@@H:18]([NH:22][C@H:23]([C:25](O)=[O:26])[CH3:24])[CH2:19][CH2:20][CH3:21])([O:15][CH2:16][CH3:17])=[O:14].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Na+].[Cl-]>C(#N)C.C(N(CC)CC)C>[CH2:16]([O:15][C:13]([C@@H:18]([NH:22][C@@H:23]([CH3:24])[C:25]([O:2][C:1]([CH:4]1[CH2:12][CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[NH:5]1)=[O:3])=[O:26])[CH2:19][CH2:20][CH3:21])=[O:14])[CH3:17]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 74084522-Carboxyoctahydroindole, (2S,3aS,7aS)-HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

Product 1

HCID 87539627HCID 87539627, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Mixture of 855 mg of benzyl ester of (2S,3aS,7aS)-2-carboxyperhydro indole, 651 mg of N-((S)-1-carbethoxybutyl)-(S)-alanine and 1137 mg of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate and 0.84 ml of triethylamine was stirred in 20 ml of acetonitrile for 30 minutes. 50 ml of saturated NaCl was added and product was extracted twice with 35 ml of EtOAc. Combined extracts were washed with 70 ml of water/1 ml of conc. HCl and than with 130 ml of waters dried with Na2SO4 and evaporated at 40° C. in vacuum. 1210 mg (87.7%) of benzyl (2S,3aS,7aS)-((2-(1-(ethoxycarbonyl)-(S)-butylamino)-(S)-propionyl)octahydroindole-2-carboxylate (benzyl ester of perindopril) was obtained.

Workup

  1. extractionproduct was extracted twice with 35 ml of EtOAc
  2. washCombined extracts were washed with 70 ml of water/1 ml of conc. HCl and than with 130 ml of waters
  3. dry with materialdried with Na2SO4
  4. customevaporated at 40° C. in vacuum

Sources & evidence

ORD record
ord-2ad1664e49dd4eb7860aee459313c176
Source dataset
uspto-grants-2010_03
Patent number
US07671215B2

Reaction notes

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