Ethyl 3-bromopropionate → HCID 131713564, compound
Reaction equation
Br[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[CH2:10]([O:17][C:18](=[O:24])[C@@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:4]([CH2:3][CH2:2][N:20]1[CH2:21][CH2:22][CH2:23][C@H:19]1[C:18]([O:17][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:24])([O:6][CH2:7][CH3:8])=[O:5]Participants
Procedure
Using the same reactions described above, 7.23 g (0.03) of ethyl β-bromopropionate and 7.33 g (0.04 m) of proline benzyl ester hydrochloride gave N-(2-carbethoxy)ethyl-L-proline, benzyl ester (4.6 g, 50.2%). This compound (4.6 g, 0.015 m) was hydrogenated over palladium-on-carbon to give 2.96 g (78%) of N-(2-carbethoxy)ethyl-L-propline, hydrochloride, m.p. 169°-171°. This compound (2.42 g, 0.0096 m) was condensed with 2.25 g (0.0072 m) of L-alanyl-L-proline, benzyl ester hydrochloride in the dicyclohexylcarbodiimide procedure to give 0.8 g of N-(2-carbethoxy)ethyl-L-prolyl-L-alanyl-L-proline, benzyl ester. The pro-drug precursor was hydrolyzed with barium hydroxide in aqueous methanol to give 0.498 g (64%) of N-(2-carboxyethyl)-L-prolyl-L-alanyl-L-proline, m.p. 133°-136°.
Sources & evidence
- ORD record
- ord-37b6f4a715ab40739dc76dfdb8b6e9fb
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04456594
Reaction notes
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