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107133-36-8

Basic Information
CAS No.: 107133-36-8
Name: Perindopril erbumine
Molecular Structure:
Molecular Structure of 107133-36-8 (Perindopril erbumine)
Formula: C19H32N2O5.C4H11N
Molecular Weight: 441.69
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
Solubility:
Appearance: white solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information:
PSA: 121.96000
LogP: 3.71330
Synthetic route
82834-16-0

Perindopril

75-64-9

tert-butylamine

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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
ConditionsYield
With hydrogenchloride; tert-butylamine; triethylamine In dichloromethane; water; acetonitrileA 81%
B n/a
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
ConditionsYield
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%

(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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In water at 20℃; for 1h; Product distribution / selectivity;

benzylperindopril oxalate

75-64-9

tert-butylamine

107133-36-8

perindopril tert-butylamine

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

(-)-di-p-toluoyl tartaric acid salt of perindopril

75-64-9

tert-butylamine

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
In water Product distribution / selectivity;

(2S)-2-[(1S)-1-carbethoxybutylamino]-1-oxopropyl-(2S,3aS,7aS)-perhydroindole-2-carboxylic acid dicyclohexylamine salt

75-64-9

tert-butylamine

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
In 2,2-dimethoxy-propane at 25 - 30℃; for 4 - 5h; Product distribution / selectivity;
at 25 - 30℃; for 4 - 5h; Product distribution / selectivity;

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

75-64-9

tert-butylamine

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Stage #1: (2S,3aS,7aS)-1-{2-[1-(ethoxycarbonyl)-(S)-butylamine]-(S)-propionyl}octahydroindole-2-carboxylic acid 4-methoxybenzyl ester With hydrogen; palladium on activated charcoal In ethyl acetate under 2068.65 Torr; for 5h;
Stage #2: tert-butylamine In ethyl acetate at 45℃; for 2h;
200423-22-9

(2S,3aS,7aS)-octahydroindole-2-carboxylic acid trimethylsilyl ester

869877-95-2

N-[1(S)-ethoxycarbonyl-1-butyl]-(S)-alanyl chloride hydrochloride

75-64-9

tert-butylamine

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Stage #1: N-[1(S)-ethoxycarbonyl-1-butyl]-(S)-alanyl chloride hydrochloride With 1H-imidazole In dichloromethane at 10 - 15℃; for 1h;
Stage #2: (2S,3aS,7aS)-octahydroindole-2-carboxylic acid trimethylsilyl ester In dichloromethane at 10℃; for 3h;
Stage #3: tert-butylamine In dichloromethane at 10 - 40℃; for 1h; Product distribution / selectivity;
869877-95-2

N-[1(S)-ethoxycarbonyl-1-butyl]-(S)-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
ConditionsYield
Stage #1: N-[1(S)-ethoxycarbonyl-1-butyl]-(S)-alanyl chloride hydrochloride With 1H-imidazole In dichloromethane at -5 - 0℃; for 1h;
Stage #2: (2S,3aS,7aS)-perhydroindole-2-carboxylic acid In dichloromethane at -5 - 25℃; for 4.75h;
Stage #3: tert-butylamine In dichloromethane at 10 - 40℃; for 1h; Product distribution / selectivity;
86647-57-6

(2S,3aS,7aS)-phenylmethyl octahydroindole-2-carboxylate hydrochloride

82834-12-6

N-<1(S)-(ethoxycarbonyl)butyl>-L-alanine

75-64-9

tert-butylamine

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Stage #1: (2S,3aS,7aS)-phenylmethyl octahydroindole-2-carboxylate hydrochloride; N-<1(S)-(ethoxycarbonyl)butyl>-L-alanine With triethylamine In Isopropyl acetate at 10 - 15℃; for 0.25h;
Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In Isopropyl acetate at -10 - 30℃; for 6h;
Stage #3: tert-butylamine With hydrogen; 5% palladium over charcoal In ethanol
79815-20-6

(S)-indoline-2-carboxylic acid

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave
2.1: triethylamine; chloro-trimethyl-silane / dichloromethane / 2 h / 20 °C / Inert atmosphere
2.2: 4 h / -5 - 5 °C
3.1: ethyl acetate / 0.5 h
View Scheme
89-98-5

2-chloro-benzaldehyde

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium acetate; acetic anhydride / 0.5 h / 20 °C / Inert atmosphere
1.2: 90 - 100 °C
2.1: sodium / 40 - 50 °C / Inert atmosphere
3.1: hydrogen; [Rhcod(S)-DuanPhos]BF4 / ethanol / 45 - 55 °C / 15001.5 Torr / Autoclave
4.1: potassium carbonate; copper(l) chloride / dimethyl sulfoxide / 100 - 105 °C / Inert atmosphere
5.1: sulfuric acid; water / Reflux
6.1: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave
7.1: triethylamine; chloro-trimethyl-silane / dichloromethane / 2 h / 20 °C / Inert atmosphere
7.2: 4 h / -5 - 5 °C
8.1: ethyl acetate / 0.5 h
View Scheme

(4Z)-4-[(2-chlorophenyl)methylene]-2-methyl-1,3-oxazol-5-one

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium / 40 - 50 °C / Inert atmosphere
2.1: hydrogen; [Rhcod(S)-DuanPhos]BF4 / ethanol / 45 - 55 °C / 15001.5 Torr / Autoclave
3.1: potassium carbonate; copper(l) chloride / dimethyl sulfoxide / 100 - 105 °C / Inert atmosphere
4.1: sulfuric acid; water / Reflux
5.1: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave
6.1: triethylamine; chloro-trimethyl-silane / dichloromethane / 2 h / 20 °C / Inert atmosphere
6.2: 4 h / -5 - 5 °C
7.1: ethyl acetate / 0.5 h
View Scheme

(Z)-2-acetylamino-3-(2-chlorophenyl)acrylic acid methyl ester

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogen; [Rhcod(S)-DuanPhos]BF4 / ethanol / 45 - 55 °C / 15001.5 Torr / Autoclave
2.1: potassium carbonate; copper(l) chloride / dimethyl sulfoxide / 100 - 105 °C / Inert atmosphere
3.1: sulfuric acid; water / Reflux
4.1: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave
5.1: triethylamine; chloro-trimethyl-silane / dichloromethane / 2 h / 20 °C / Inert atmosphere
5.2: 4 h / -5 - 5 °C
6.1: ethyl acetate / 0.5 h
View Scheme

methyl (S)-2-acetamido-3-(2-chlorophenyl)propionate

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate; copper(l) chloride / dimethyl sulfoxide / 100 - 105 °C / Inert atmosphere
2.1: sulfuric acid; water / Reflux
3.1: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave
4.1: triethylamine; chloro-trimethyl-silane / dichloromethane / 2 h / 20 °C / Inert atmosphere
4.2: 4 h / -5 - 5 °C
5.1: ethyl acetate / 0.5 h
View Scheme
110592-39-7

(S)-N-acetyl-2,3-dihydroindoline-2-carboxylic acid methyl ester

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sulfuric acid; water / Reflux
2.1: hydrogen; 8 % Pd/C / methanol / 55 - 65 °C / 37503.8 Torr / Autoclave
3.1: triethylamine; chloro-trimethyl-silane / dichloromethane / 2 h / 20 °C / Inert atmosphere
3.2: 4 h / -5 - 5 °C
4.1: ethyl acetate / 0.5 h
View Scheme
80875-98-5

(2S,3aS,7aS)-perhydroindole-2-carboxylic acid

107133-36-8

perindopril tert-butylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; chloro-trimethyl-silane / dichloromethane / 2 h / 20 °C / Inert atmosphere
1.2: 4 h / -5 - 5 °C
2.1: ethyl acetate / 0.5 h
View Scheme
107133-36-8

perindopril tert-butylamine

2-methylpropane-2-amine-(2S,3aS,7aS)-1-[(2S)-2-[(1S)-1-ethoxycarbonyl-butylamino]propanoyl]octahydro-1H-indole-2-carboxylate monohydrate

Conditions
ConditionsYield
With water In acetone at -80℃;100%
107133-36-8

perindopril tert-butylamine

2-methylpropane-2-amine-(2S,3aS,7aS)-1-[(2S)-2-[(1S)-1-ethoxycarbonyl-butylamino]propanoyl]octahydro-1H-indole-2-carboxylate dihydrate

Conditions
ConditionsYield
With water at 30 - 40℃; for 240h; Product distribution / selectivity;100%
With water In acetonitrile at -50 - -45℃; Product distribution / selectivity;
74-79-3

L-arginine

107133-36-8

perindopril tert-butylamine

612548-45-5

perindopril L-arginine

Conditions
ConditionsYield
With methanesulfonic acid In dimethyl sulfoxide at 70℃; for 1h;88%
107133-36-8

perindopril tert-butylamine

82834-16-0

Perindopril

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 10 - 30℃; for 0.5h; Product distribution / selectivity;80%
With hydrogenchloride In dichloromethane; water pH=5.4; Product distribution / selectivity;
Stage #1: perindopril tert-butylamine With sulfuric acid In ethanol at 20 - 25℃; for 1.5h;
Stage #2: With sodium hydroxide In dichloromethane; water pH=4.2; Product distribution / selectivity;
With calcium chloride In ethyl acetate Product distribution / selectivity; Heating / reflux;
107133-36-8

perindopril tert-butylamine

95153-31-4

perindoprilat

Conditions
ConditionsYield
With sodium hydroxide for 72h; Ambient temperature;75%
With water; 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide at 59.84℃; for 120h; Kinetics;
107133-36-8

perindopril tert-butylamine

A

129970-98-5

ethyl (2S)-2-[(3S,5aS,9aS,10aS)-3-methyl-1,4-dioxo-5a,6,7,8,9,9a,10,10a-octahydro-3H-pyrazino[1,2-a]indol-2-yl]pentanoate

B

95153-31-4

perindoprilat

Conditions
ConditionsYield
With water at 40℃; Conversion of starting material;A 0.04%
B 0.03%
107133-36-8

perindopril tert-butylamine

67-68-5

dimethyl sulfoxide

97-00-7

1-chloro-2,4-dinitro-benzene

C19H31N2O5*C8H9ClN2O5S

Conditions
ConditionsYield
at 30℃; Activation energy; Further Variations:; Temperatures;
107133-36-8

perindopril tert-butylamine

2-methylpropane-2-amine-(2S,3aS,7aS)-1-[(2S)-2-[(1S)-1-ethoxycarbonyl-butylamino]propanoyl]octahydro-1H-indole-2-carboxylate sesquihydrate

Conditions
ConditionsYield
With water at -15℃; for 1h; Product distribution / selectivity;
111-87-5

octanol

107133-36-8

perindopril tert-butylamine

(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid tert-butylamine salt octanol solvate

Conditions
ConditionsYield
In ethyl acetate at 30 - 60℃;
111-70-6

n-heptan1ol

107133-36-8

perindopril tert-butylamine

(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid tert-butylamine salt heptanol solvate

Conditions
ConditionsYield
In toluene at 20 - 55℃;
107133-36-8

perindopril tert-butylamine

108-93-0

cyclohexanol

(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid tert-butylamine salt cyclohexanol solvate

Conditions
ConditionsYield
In toluene at 20 - 65℃;
at 20 - 60℃; Product distribution / selectivity;
71-41-0

pentan-1-ol

107133-36-8

perindopril tert-butylamine

(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid tert-butylamine salt pentanol solvate

Conditions
ConditionsYield
In ethyl acetate at 20 - 60℃;
107133-36-8

perindopril tert-butylamine

calcium chloride

calcium salt of perindopril

Conditions
ConditionsYield
In ethyl acetate Heating / reflux;
Downstream Products
95153-31-4
82834-16-0
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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 NOx Hazard codes: XiIrritant
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