Captopril → 1-[(2S)-3-[(3-(nitrooxy)propyl) carbonylthio]-2-methyl-1-oxopropyl]-L-proline

HRID 2241112Notes

Reaction equation

HRID 2241112 reaction equation
[SH:1][CH2:2][C@@H:3]([CH3:14])[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5].FC1C([O:22][C:23](=O)[CH2:24][CH2:25][CH2:26][O:27][N+:28]([O-:30])=[O:29])=C(F)C(F)=C(F)C=1F>CN(C1C=CN=CC=1)C>[N+:28]([O:27][CH2:26][CH2:25][CH2:24][C:23]([S:1][CH2:2][C@@H:3]([CH3:14])[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])=[O:22])([O-:30])=[O:29]

Participants

4

Reactant 2

HCID 44093CaptoprilHCID 11522541Perfluorophenyl 4-(nitrooxy)butanoate

Product 1

HCID 113254981-[(2S)-3-[(3-(nitrooxy)propyl) carbonylthio]-2-methyl-1-oxopropyl]-L-proline

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Using the same procedure described in Example 1 but starting from 1-[(2S)-3-mercapto-2-methyl-1-oxopropyl]-L-proline (Captopril)(0.41 g, 1.9 mmol), 4-(nitrooxy)butanoic acid pentafluorophenyl ester (0.60 g, 1.9 mmol) TEA (0.26 ml, 1.9 mmol) and DMAP (0.23 g, 1.9 mmol) after purification with Flash chromatography of the residue (CH2Cl2/Acetone 80:20) the title compound (0.140 g, 20%) was obtained as a white foam.

Workup

  1. customafter purification with Flash chromatography of the residue (CH2Cl2/Acetone 80:20) the title compound (0.140 g, 20%)
  2. customwas obtained as a white foam

Sources & evidence

ORD record
ord-ef5034f0768148feb9410f351c921c47
Source dataset
uspto-grants-2010_05
Patent number
US07723529B2

Reaction notes

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