Captopril → HCID 86595502, compound

HRID 1375694Notes

Reaction equation

HRID 1375694 reaction equation
[CH3:1][C@@H:2]([C:5]([N:7]1[C@H:11]([C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8]1)=[O:6])[CH2:3][SH:4].C(N(CC)C(C)C)(C)C.Cl[C:25]([O:27][CH2:28][Cl:29])=[O:26]>O1CCOCC1.O>[Cl:29][CH2:28][O:27][C:25]([S:4][CH2:3][C@@H:2]([CH3:1])[C:5]([N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]1[C:12]([OH:14])=[O:13])=[O:6])=[O:26]

Participants

5

Reactant 3

HCID 44093CaptoprilHCID 62754Chloromethyl chloroformateHCID 81531Diisopropylethylamine

Product 1

HCID 86595502HCID 86595502, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

Captopril (2.48 g, 0.0114 Mol) and N,N-diisopropyl ethylamine (4.50 ml, 0.0258 Mol) were dissolved in dioxane/H2O (30 ml, 1:1). The mixture was cooled to 0° C. and 1-chloromethyl chloroformate (1.20 ml, 0.0147 Mol) was added. The reaction was stirred at 0° C. for 4 h, then partitioned between HCl (4%, 30 ml) and CH2Cl2 (30 ml). The aqueous phase was extracted with CH2Cl2 (2×30 ml) and the combined organic phases were washed with HCl (4%, 30 ml) and brine (3×30 ml), dried over sodium sulphate and evaporated under reduced pressure affording 1-[(2S)-3-(chloromethoxycarbonyl)mercapto-2-methyl-1-oxopropyl]-L-proline as a clear oil (2.60 g) that was used without further purification.

Workup

  1. custompartitioned between HCl (4%, 30 ml) and CH2Cl2 (30 ml)
  2. extractionThe aqueous phase was extracted with CH2Cl2 (2×30 ml)
  3. washthe combined organic phases were washed with HCl (4%, 30 ml) and brine (3×30 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c54f1a99a46344b08eb3935540439851
Source dataset
uspto-grants-2007_01
Patent number
US07169805B2

Reaction notes

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