Sodium Chloride → Enalapril

HRID 2242530

Reaction equation

HRID 2242530 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([NH:15][C@H:16]([C:18]([OH:20])=O)[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].[NH:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([OH:25])=[O:24].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.CN(C=O)C.C(N(CC)CC)C>[CH3:2][CH2:1][O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:21]1[C@H:22]([C:23]([OH:25])=[O:24])[CH2:26][CH2:27][CH2:28]1)=[O:20])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 145742L-ProlineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13044262N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine

Product 1

HCID 5388962Enalapril

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

2.9 ml triethylamine was added to the mixture of 2.79 g of 1-((S)—N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanine and 1.15 g of L-proline in 100 ml of acetonitrile and 5 ml DMF and during stirring 3.8 g O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate was added. The reaction mixture was stirred for further 30 minutes at room temperature. 300 ml of saturated NaCl solution was added and the mixture was extracted twice with 100 ml of ethyl acetate. Combined extracts were washed with 70 ml of water/1 ml of conc. HCl mixture and then with 130 ml of water, dried with Na2SO4 and evaporated at 40° C. in vacuum. 3.55 g of enalapril was obtained.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted twice with 100 ml of ethyl acetate
  3. washCombined extracts were washed with 70 ml of water/1 ml of conc. HCl mixture
  4. dry with materialwith 130 ml of water, dried with Na2SO4
  5. customevaporated at 40° C. in vacuum

Sources & evidence

ORD record
ord-59f5c79f793146ffb64f39a00dd9ca49
Source dataset
uspto-grants-2010_03
Patent number
US07671215B2

Linked notes

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