Name: Perindopril erbumine
SKU: 107133-36-8

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Basic Information

Molecular Structure:
CAS No.:	107133-36-8
Name:	Perindopril erbumine

Formula:	C₁₉H₃₂N₂O₅^.C₄H₁₁N
Molecular Weight:	441.612
Synonyms:	(2S,3aS,7aS)-1-((S)-N-((S)-1-Carboxybutyl)alanyl)hexahydro-2-indolinecarboxylic acid, 1-ethyl ester, compound with tert-butylamine (1:1);Aceon (TN);S 9490-3;Perindopril erbumine/tert-butylamine;Perindopril erbumine [USAN];(2S,3aS,7aS)-1-{(2S)-2-[(1S)-1-(ethoxycarbonyl)butylamino]propanoyl}octahydro-1H-indole-2-carboxylic acid--2-methylpropan-2-amine (1/1);(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-ethoxycarbonylbutyl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid; 2-methylpropan-2-amine;S-9490-3;1H-Indole-2-carboxylic acid,1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)- butyl]amino]-1-oxopropyl]octahydro-,(2S,3aS,- 7aS)-,compd. with 2-methyl-2-propanamine (1:1);1H-Indole-2-carboxylic acid, 1-(2-((1-(ethoxycarbonyl)butyl)amino)-1-oxopropyl)octahydro-, (2S-(1(R(R)),2alpha,3abeta,7abeta))-, compd. with 2-methyl-2-propanamine (1:1);McN-A-2833-109;Perindopril erbumine (JAN/USAN);MCN-A 2833-109;Perindopril tert-butylamine;Perindopril;
EINECS:	600-798-6
Density:	1.15 g/cm³
Melting Point:	126-128 °C
Boiling Point:	537.4 °C at 760 mmHg
Flash Point:	278.8 °C
Appearance:	white solid
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
PSA:	121.96000
LogP:	3.71330

Synthetic route

: 82834-16-0
Perindopril

: 75-64-9
tert-butylamine

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
In ethyl acetate Heating / reflux;	95%
In ethyl acetate Heating / reflux;	95%
In ethyl acetate Heating / reflux;	95%

: 82834-16-0
Perindopril

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
With tert-butylamine In ethyl acetate; acetonitrile Heating / reflux;	95%
With tert-butylamine In ethyl acetate at 20℃; for 1 - 1.5h;	65%

: 75-64-9
tert-butylamine

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
Stage #1: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With tert-butylimino-tri(pyrrolidino)phosphorane In acetonitrile Stage #2: N-[1(S)-(ethoxycarbonyl)butyl]-L-alanine ester of acetonoxime In acetonitrile at 50℃; for 0.5h; Stage #3: tert-butylamine In dichloromethane at 0 - 10℃; for 0.5h; Product distribution / selectivity;	90%
Stage #1: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Stage #2: N-[1(S)-(ethoxycarbonyl)butyl]-L-alanine ester of acetonoxime In acetonitrile at 40 - 45℃; Stage #3: tert-butylamine With hydrogenchloride In acetonitrile at 50 - 60℃; Product distribution / selectivity;	90%
Stage #1: benzylperindopril oxalate With hydrogen; 5%-palladium/activated carbon In ethanol at 30℃; under 3677.86 Torr; for 3h; Stage #2: tert-butylamine In ethanol Product distribution / selectivity;

: N-((S)-1-carbethoxybutyl)-L-alanyl chloride hydrochloride

: 80875-98-5
(2S,3aS,7aS)-perhydroindole-2-carboxylic acid

: 75-64-9
tert-butylamine

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
Stage #1: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With chloro-trimethyl-silane; triethylamine In dichloromethane at 20 - 25℃; for 2h; Stage #2: N-((S)-1-carbethoxybutyl)-L-alanyl chloride hydrochloride With triethylamine In dichloromethane at -15℃; for 2h; Stage #3: tert-butylamine In Isopropyl acetate Product distribution / selectivity;	86%
Stage #1: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With chloro-trimethyl-silane; triethylamine In dichloromethane at 20 - 25℃; for 2h; Stage #2: N-((S)-1-carbethoxybutyl)-L-alanyl chloride hydrochloride With triethylamine In dichloromethane at -15℃; for 2h; Stage #3: tert-butylamine In ethyl acetate Product distribution / selectivity;	80%
Stage #1: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid With chloro-trimethyl-silane; triethylamine In dichloromethane at 20 - 25℃; for 2h; Stage #2: N-((S)-1-carbethoxybutyl)-L-alanyl chloride hydrochloride With triethylamine In dichloromethane at -15℃; for 2h; Stage #3: tert-butylamine In DMF (N,N-dimethyl-formamide) Product distribution / selectivity;	78%

...Expand

: 2,5-dioxo-3-[1-(S)-ethoxycarbonyl-butyl]-4-(S)-methyl-oxazolidine

: 82717-40-6
octahydro-1H-indole-2-carboxylic acid

A tert-butylamine (2S,3AS,7AS)-1-{2-[1-ethoxycarbonyl)-(S)-butylamino]-(S)-propionyl}-octahydroindol-2-carboxylate: tert-butylamine (2S,3AS,7AS)-1-{2-[1-ethoxycarbonyl)-(S)-butylamino]-(S)-propionyl}-octahydroindol-2-carboxylate

B: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
With hydrogenchloride; tert-butylamine; triethylamine In dichloromethane; water; acetonitrile	A 81% B n/a

...Expand

: 1159491-00-5
C12H23NO2Si

: 82834-12-6
N-<1(S)-(ethoxycarbonyl)butyl>-L-alanine

: 75-64-9
tert-butylamine

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
Stage #1: N-<1(S)-(ethoxycarbonyl)butyl>-L-alanine With 1H-imidazole; thionyl chloride In dichloromethane at -10℃; for 2h; Stage #2: C12H23NO2Si In dichloromethane at -10 - 25℃; for 21h; Stage #3: tert-butylamine In acetonitrile Heating / reflux;	61%

...Expand

: (2S,3aS,7aS)-1-{2-[1-(ethoxycarbonyl)-(S)-butylamine]-(S)-propionyl}octahydroindole-2-carboxylic acid 4-chlorobenzyl ester

: 75-64-9
tert-butylamine

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate under 2068.65 Torr; for 8h;

: perindopril oxalate

: 75-64-9
tert-butylamine

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
In dichloromethane Product distribution / selectivity;
In water Product distribution / selectivity;

: phosphate salt of perindopril

: 75-64-9
tert-butylamine

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
In water at 20℃; for 1h; Product distribution / selectivity;

: benzylperindopril oxalate

: 75-64-9
tert-butylamine

: 107133-36-8
perindopril tert-butylamine

Conditions

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In ethanol at 30℃; under 3677.86 Torr; for 3h; Product distribution / selectivity;

Raw Materials

75-64-9

Downstream Products

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Chemistry

The Molecular Structure of Perindopril erbumine (CAS NO.107133-36-8):

Empirical Formula: C₁₉H₃₂N₂O₅
Molecular Weight: 368.4678
Nominal Mass: 368 Da
Average Mass: 368.4678 Da
Monoisotopic Mass: 368.231122 Da
Index of Refraction: 1.512
Molar Refractivity: 96.17 cm³
Molar Volume: 320.3 cm³
Surface Tension: 44.9 dyne/cm
Density: 1.15 g/cm³
Flash Point: 278.8 °C
Enthalpy of Vaporization: 89.06 kJ/mol
Boiling Point: 537.4 °C at 760 mmHg
Vapour Pressure: 5.63E-13 mmHg at 25°C
Synonyms: Perindopril ; Perindopril erbumine [USAN] ; (2S,3aS,7aS)-1-((S)-N-((S)-1-Carboxybutyl)alanyl)hexahydro-2-indolinecarboxylic acid, 1-ethyl ester, compound with
tert-butylamine (1:1) ; ACEON ; McN-A-2833-109 ; Perindopril erbumine ; Perindopril tert-butylamine ; S-9490-3 ; UNII-1964X464OJ ; 1H-Indole-2-carboxylic acid, 1-(2-((1-
(ethoxycarbonyl)butyl)amino)-1-oxopropyl)octahydro-, (2S-(1(R*(R*)),2alpha,3abeta,7abeta))-, compd. with 2-methyl-2-propanamine (1:1)

Uses

Perindopril erbumine (CAS NO.107133-36-8) can be used as anangiotensin-converting enzyme (ACE) inhibitor.

Toxicity Data With Reference

1.	orl-rat LD :>2500 mg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),3147.
2.	ivn-rat LD50:323 mg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),3147.
3.	orl-mus LD :>2500 mg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),3147.
4.	ivn-mus LD50:323 mg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 40 (1998),3147.

Safety Profile

A poison by intravenous route. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NO_xHazard codes: Xi Irritant
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing

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Chemistry

Uses

Toxicity Data With Reference

Safety Profile