(S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester → Spirapril

HRID 1463036Notes

Reaction equation

HRID 1463036 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]([CH3:44])[C:17]([N:19]1[C@H:27]([C:28]([O:30]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:29])[CH2:26][C:21]2([S:25][CH2:24][CH2:23][S:22]2)[CH2:20]1)=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]([CH3:44])[C:17]([N:19]1[C@H:27]([C:28]([OH:30])=[O:29])[CH2:26][C:21]2([S:22][CH2:23][CH2:24][S:25]2)[CH2:20]1)=[O:18])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 86739578(S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester

Product 1

HCID 5311447Spirapril

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of (S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester (800 mg.) in a mixture of trifluoroacetic acid (15 ml.) and anisole (3 ml.) is stirred at 0° for 30 minutes. The solvent is removed at reduced pressure and the residue applied to an AG 50W-X2(H+) column. After washing with water, the column is eluted with aqueous pyridine. The fractions containing the product are combined and lyophilized to yield (S,S,S)-7-[2-[(1-ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid.

Workup

  1. customThe solvent is removed at reduced pressure
  2. washAfter washing with water
  3. washthe column is eluted with aqueous pyridine
  4. additionThe fractions containing the product

Sources & evidence

ORD record
ord-bed9253f9b5b40d3a4f3d2d5bd406be6
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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