Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 87539627, compound

HRID 2076335Notes

Reaction equation

HRID 2076335 reaction equation
[C:1]([C@@H:6]([NH:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12])[CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2].F[P-](F)(F)(F)(F)F.[N:23]1(OC(N(C)C)=[N+](C)C)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2N=N1>C(#N)C.[Cl-].[Na+].O>[CH2:4]([O:3][C:1]([C@@H:6]([NH:10][C@@H:11]([CH3:12])[C:13]([O:15][C:1]([CH:6]1[CH2:7][CH:26]2[CH:27]([CH2:28][CH2:29][CH2:30][CH2:31]2)[NH:23]1)=[O:2])=[O:14])[CH2:7][CH2:8][CH3:9])=[O:2])[CH3:5]

Participants

5

Reactant 2

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)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 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 9.54 g of (2S,3aS,7aS)-2-carboxyperhydroindole benzyl ester, 7.26 g of N-((S)-1-carbetoxybutyl)-(S)-alanine and 12.7 g of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate in 225 ml of acetonitrile is stirred at room temperature for 30 min, then 560 ml of brine is added. The product is extracted twice with 400 ml of ethyl acetate, combined extracts are washed first with 800 ml of water, acidified with concentrated hydrochloric acid and then with 1.5 l of water. Organic phase is dried over anhydrous sodium sulphate and evaporated at 40° C. in vacuo to yield 13.5 g (88%) of benzyl (2S,3aS,7aS)-((2-(1-(ethoxycarbonyl)-(S)-butylamino)-(S)-propionyl)octahydroindole-2-carboxylate (benzyl ester of perindopril).

Workup

  1. extractionThe product is extracted twice with 400 ml of ethyl acetate
  2. washare washed first with 800 ml of water
  3. dry with materialOrganic phase is dried over anhydrous sodium sulphate
  4. customevaporated at 40° C. in vacuo

Sources & evidence

ORD record
ord-556d77a3610d486885110509932a82e1
Source dataset
uspto-grants-2011_04
Patent number
US07923570B2

Reaction notes

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