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Captopril (3.50 g, 0.0161 Mol) and N,N-diisopropyl ethylamine (6.80 ml, 0.039 Mol) were dissolved in H2O/CH3CN (80 ml, 1:1) and the mixture was cooled to 0° C. Then 4-chlorobutylchloroformate (2.70 ml, 0.0198 Mol) was added and the reaction was slowly warmed to room temperature and stirred for 4 h. The mixture was then partitioned between HCl (4%, 100 ml) and EtOAc (100 ml). The organic layer was separated and the aqueous phase was extracted with EtOAc (2×100 ml). The combined organic phases were washed with brine (3×60 ml), dried over sodium sulphate and evaporated under reduced pressure affording 1-[(2S)-3-(4-chlorobutoxycarbonyl)mercapto-2-methyl-1-oxopropyl]-L-proline (5.90 g) as a colourless oil that was used without further purification.

1. temperaturethe reaction was slowly warmed to room temperature
2. customThe mixture was then partitioned between HCl (4%, 100 ml) and EtOAc (100 ml)
3. customThe organic layer was separated
4. extractionthe aqueous phase was extracted with EtOAc (2×100 ml)
5. washThe combined organic phases were washed with brine (3×60 ml)
6. dry with materialdried over sodium sulphate
7. customevaporated under reduced pressure