ChemicalBook CAS DataBase List 2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER

2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER synthesis

6synthesis methods

Product Name:2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER
CAS Number:87269-88-3
Molecular formula:C30H38N2O5
Molecular Weight:506.63

Benzenebutanoic acid, α-[[(1S)-2-chloro-1-methyl-2-oxoethyl]amino]-, ethyl ester, hydrochloride (αS)-

114192-42-6
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Cyclopenta[b]pyrrole-2-carboxylic acid, octahydro-, (2S,3aS,6aS)-, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

852546-84-0
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2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER

87269-88-3
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Yield:-

Reaction Conditions:

Stage #1: (2S,3aS,6aS)-benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate 4-toluenesulfonate (1:1)with triethylamine in dichloromethane at 0; for 0.5 h;
Stage #2: N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloridewith 1H-imidazole in dichloromethane at 0 - 20; for 4.5 h;

Steps:

9

Example 9; Preparation of (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid,1 -[(2S)-2-[[(1 S)-1 -(ethoxycarbonyl)-3-phenylpropyl]amino]-1 -oxopropyl], phenylmethyl ester from (2S,3aS,6aS)-benzyl octahydrocyclopenta[b]pyrrole-2- carboxylate; The toluenesulfonate salt prepared in Example 7 (6.00 g, 14.4 mmol) was suspended in CH₂CI₂ (60 ml.) and triethylamine (1.46 g, 14.4 mmol) was added at 0⁰C. The slurry was stirred for 30 min and then imidazole (2.94 g, 43.1 mmol) was added in small portions, followed by N-[(S)-1-(ethoxycarbonyl)-3-phenyl-propyl]-L-alanylchloride HCI prepared in Example 8 (5.28 g ,15.8 mmol). The reaction mixture was stirred for 2 h at 0⁰C and then allowed to warm to 20⁰C within 30 min and stirred at that temperature for 2 h. Water (60 ml.) was then added and after vigorous mixing of the phases, the organic layer was separated and the aqueous layer was extracted once more with CH₂Cb (60 ml_). The combined organic layers were washed with aqueous saturated NaHCO₃ (60 ml_), treated with charcoal (1 g) and dried over anhydrous Na₂SO₄ (5 g). After filtration of the salt and evaporation of the solvent in vacuo at 40⁰C, the product was obtained as a yellowish oil. This oil was redissolved in methanol (90 ml.) and 5% Pd/C (0.50 g) was added and hydrogenation was performed under 2 bar of hydrogen pressure. After approx. 4 h, consumption of hydrogen ceased and the catalyst was filtered off on a pad of celite. Additional methanol was used to wash the celite (20 ml_). The organic layer was removed in vacuo at 50⁰C. The residue was recrystallized from ethyl ether (100 ml.) at 0°C. The product ramipril ([9], p = 1 , R₄ = phenyl) is a colorless solid. Weight 4.56 g, 70% yield.