33208-99-0

Basic information

• Product Name: L-Alaninamide hydrochloride
• Synonyms: (S)-2-AMINOPROPIONAMIDE HYDROCHLORIDE;L-ALANAMINE HCL;(L)-ALANINAMIDE HCL;L-ALANINAMIDE HYDROCHLORIDE;L-ALANINE AMIDE HYDROCHLORIDE;H-L-ALA-NH2 HCL;H-ALA-NH2 HCL;H-ALA-NH2 HYDROCHLORIDE
• CAS NO: 33208-99-0
• Molecular Formula: C₃H₉N₂O*Cl
• Molecular Weight: 124.57
• EINECS: 608-843-1
• Product Categories: chiral;Amino Acids;Alanine [Ala, A];Amino hydrochloride;Alanine;Amino Acid Derivatives;Peptide Synthesis
• Mol File: 33208-99-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 212-217°C
• Boiling Point: 247.4 °C at 760 mmHg
• Flash Point: 103.4 °C
• Appearance: /Solid
• Vapor Pressure: 0.00555mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water
• CAS DataBase Reference: L-Alaninamide hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alaninamide hydrochloride(33208-99-0)
• EPA Substance Registry System: L-Alaninamide hydrochloride(33208-99-0)

Safety Data

• Hazard Codes: C
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 33208-99-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

L-Alaninamide hydrochloride is used for preparation of novel amide derivatives of steroidal[3,2-c]pyrazole compounds with glucocorticoid activity.

InChI:InChI=1/C3H8N2O.ClH/c1-2(4)3(5)6;/h2H,4H2,1H3,(H2,5,6);1H

Synthetic route

rac-Ala-OH (302-72-7) → (S)-alaninamide hydrochloride (33208-99-0) + D-alaninamide hydrochloride (71810-97-4)

Conditions	Yield
With laccase; ammonia In water at 38 - 40℃; Temperature; Enzymatic reaction;	A 92% B n/a

tert-butyl (1S)-2-amino-1-methyl-2-oxoethylcarbamate (78981-25-6, 81587-17-9, 85642-13-3) → (S)-alaninamide hydrochloride (33208-99-0)

Conditions	Yield
With acetyl chloride In ethanol; ethyl acetate for 1h;	80%
With hydrogenchloride In 1,4-dioxane at 80℃; for 4h;

L-alanine methyl ester hydrochloride (2491-20-5) → (S)-alaninamide hydrochloride (33208-99-0)

Conditions	Yield
With ammonia In methanol for 72h; Ambient temperature;
Stage #1: L-alanine methyl ester hydrochloride With ammonia at 20℃; for 20h; Sealed tube; Large scale; Stage #2: With hydrogenchloride In water pH=1.55; pH-value; Large scale;	85 g

3-Phenylbutyraldehyde (16251-77-7) + (S)-alaninamide hydrochloride (33208-99-0) → (5S)-5-methyl-2-(2-phenylpropyl)imidazolidin-4-one (1084907-53-8)

Conditions	Yield
With potassium carbonate; triethylamine In ethanol at 60℃; for 24h;	100%
With potassium carbonate; triethylamine In ethanol at 60℃; for 24h; Inert atmosphere;	100%

AbzBB-OPfp + (S)-alaninamide hydrochloride (33208-99-0) → (2S)-2-(4-hydroxy-2-oxo-1,4-dihydroquinazolin-3(2H)-yl)propanamide

Conditions	Yield
With N-ethylmorpholine; In N,N-dimethyl-formamide at 20℃;	100%

(S)-alaninamide hydrochloride (33208-99-0) + (2S,2'S)-4,4'-disulfanediylbis(2-(tert-butoxycarbonyl)amino)butanoic acid (130981-51-0) → (Boc-Hcy-Ala-NH2)2 (569341-03-3)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h;	99%

BOC-L-aspartic acid 4-benzyl ester (7536-58-5) + (S)-alaninamide hydrochloride (33208-99-0) → BOC-Asp(OBn)-Ala-NH2 (302911-12-2)

Conditions	Yield
Stage #1: BOC-L-aspartic acid 4-benzyl ester With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran; N,N-dimethyl-formamide at -40 - 0℃; for 1h; Stage #2: (S)-alaninamide hydrochloride With 4-methyl-morpholine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 24h;	99%

3-((quinoline-8-oxy)methyl)benzaldehyde + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-((3-((quinolin-8-yloxy)methyl)benzyl)amino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 0.5h; Stage #2: 3-((quinoline-8-oxy)methyl)benzaldehyde In methanol at 20℃; for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	96.08%
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 1h; Stage #2: 3-((quinoline-8-oxy)methyl)benzaldehyde In methanol for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	96%

benzyloxycarbonyl-L-leucine benzyl ester (124980-31-0) + (S)-alaninamide hydrochloride (33208-99-0) → Cbz-Leu-Ala-NH2 (62074-75-3)

Conditions	Yield
With Alcalase In tert-Amyl alcohol at 5℃; for 96h; Condensation;	96%

N-α-tert-butyloxycarbonyl-N-ε-benzyloxycarbonyl-lysine p-nitrophenyl ester (2389-46-0) + (S)-alaninamide hydrochloride (33208-99-0) → Nα-BOC-Nε-CBZ-L-lysyl-L-alanine amide (163848-14-4)

Conditions	Yield
With triethylamine In ethyl acetate; N,N-dimethyl-formamide	96%

2,2,2-trifluoroethyl chloroformate (27746-99-2) + (S)-alaninamide hydrochloride (33208-99-0) → N-(2,2,2-trifluoroethoxycarbonyl)-L-alaninamide (951242-82-3)

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 2.5h;	95%

3-chloro-5-(trifluoromethyl)benzoic acid (53985-49-2) + (S)-alaninamide hydrochloride (33208-99-0) → N-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-(trifluoromethyl)benzamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide for 0.5h;	95%

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + (S)-alaninamide hydrochloride (33208-99-0) → N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With magnesium sulfate; sodium hydroxide In water; acetone at 20℃; for 4h; Stage #2: 1,5-difluoro-2,4-dinitrobenzene In water; acetone at 1℃; for 20h;	93%
Stage #1: (S)-alaninamide hydrochloride With magnesium sulfate; sodium hydroxide In acetone at 20℃; for 3h; Stage #2: 1,5-difluoro-2,4-dinitrobenzene In acetone for 0.5h;	63%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-((5-(benzyloxy)-1H-indol-3-yl)methylamino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With sodium cyanoborohydride In methanol at 20℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #2: 5-benzyloxyindole-3-carboxaldehyde In methanol at 20 - 35℃; for 4h; Inert atmosphere;	92.1%

4-((2-fluorobenzyl)oxy)benzaldehyde (70627-20-2) + (S)-alaninamide hydrochloride (33208-99-0) → ralfinamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; Stage #2: 4-((2-fluorobenzyl)oxy)benzaldehyde In methanol at 25℃; for 3.33333h; Stage #3: With sodium hydroxide; sodium tetrahydroborate In methanol; water at 8℃; for 4h; Product distribution / selectivity;	92%
Stage #1: 4-((2-fluorobenzyl)oxy)benzaldehyde; (S)-alaninamide hydrochloride With triethylamine In methanol at 20 - 25℃; for 1h; Stage #2: With hydrogen; 5 % platinum on carbon In methanol at 20 - 35℃; under 3750.38 Torr; for 5h; Product distribution / selectivity;	85%
Stage #1: 4-((2-fluorobenzyl)oxy)benzaldehyde; (S)-alaninamide hydrochloride With triethylamine In methanol at 20 - 25℃; for 1h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol at 20 - 35℃; under 3750.38 Torr; for 5h; Product distribution / selectivity;	70%

(S)-alaninamide hydrochloride (33208-99-0) + N,N'-disuccinimidyl-2,2'-dithiosalicylate (497262-13-2) → N,N'-(2,2'-dithiobisbenzoyl)-bis-L-alaninamide (449775-52-4)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	92%
With triethylamine In N,N-dimethyl-formamide at 25℃;

(S)-alaninamide hydrochloride (33208-99-0) + (S)-6-trifluoroacetylamino-2-(tert-butoxycarbonylamino)-hexanoic acid (96561-04-5, 16965-06-3) → Boc-L-Lys(COCF3)-L-Ala-NH2 (1382351-57-6)

Conditions	Yield
With cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 2h; optical yield given as %de;	92%

1-bromomethyl o-carborane + (S)-alaninamide hydrochloride (33208-99-0) → C6H21B10N2O

Conditions	Yield
With 1-butyl-2,3-dimethylimidazolium tetrafluoroborate; triethylamine at 60 - 70℃; for 6h; Reagent/catalyst;	92%

4-((2,3-dihydrobenzo[b]thiophen-7-oxy)methyl)benzaldehyde + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-(4-((2,3-dihydrobenzo[b]thiophen-7-oxy)methyl)benzylamino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 0.5h; Stage #2: 4-((2,3-dihydrobenzo[b]thiophen-7-oxy)methyl)benzaldehyde In methanol at 20℃; for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	91.67%

3-((benzofuran-4-oxy)methyl) benzaldehyde + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-((3-((benzofuran-4-yloxy)methyl)benzyl)amino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 1h; Stage #2: 3-((benzofuran-4-oxy)methyl) benzaldehyde In methanol at 20℃; for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	91.18%
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 1h; Stage #2: 3-((benzofuran-4-oxy)methyl) benzaldehyde In methanol for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	91%

Cbz-Tyr-OH (1164-16-5) + (S)-alaninamide hydrochloride (33208-99-0) → Z-Tyr-Ala-NH2 (35807-79-5)

Conditions	Yield
With sodium hydroxide; δ-chymotrypsin In hydrogenchloride for 168h; Ambient temperature;	91%

4-((benzofuran-4-oxy)methyl)benzaldehyde + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-((4-((benzofuran-4-yloxy)methyl)benzyl)amino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 1h; Stage #2: 4-((benzofuran-4-oxy)methyl)benzaldehyde In methanol for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	91%
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 1h; Stage #2: 4-((benzofuran-4-oxy)methyl)benzaldehyde In methanol at 20℃; for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	55.91%

di-tert-butyl dicarbonate (24424-99-5) + (S)-alaninamide hydrochloride (33208-99-0) → tert-butyl (1S)-2-amino-1-methyl-2-oxoethylcarbamate (78981-25-6, 81587-17-9, 85642-13-3)

Conditions	Yield
With triethylamine In methanol for 12h;	90%
With triethylamine In dichloromethane for 3h;	74%
With triethylamine In tetrahydrofuran; water at 20℃; for 16h;	73%
With triethylamine In tetrahydrofuran; water at 20℃; for 16h;	73%
With sodium carbonate In 1,4-dioxane; water for 15h;

(S)-alaninamide hydrochloride (33208-99-0) + p-methoxybenzyloxycarbonyl-Phe-OMe (97985-98-3) → Moz-Phe-Ala-NH2 (145126-20-1)

Conditions	Yield
With Alcalase In tert-Amyl alcohol at 5℃; for 48h; Condensation;	90%
With triethylamine In tert-butyl alcohol at 35℃; industrial alkaline protease alcalase, 3 to 4 h;	86%

4-(3-fluoro-benzyloxy)-benzaldehyde (66742-57-2) + (S)-alaninamide hydrochloride (33208-99-0) → safinamide (133865-89-1)

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 30℃; for 0.166667h; Stage #2: 4-(3-fluoro-benzyloxy)-benzaldehyde In methanol at 20℃; for 3.5h; Stage #3: With sodium tetrahydroborate In methanol at 5℃; for 2h; Product distribution / selectivity;	90%
Stage #1: 4-(3-fluoro-benzyloxy)-benzaldehyde; (S)-alaninamide hydrochloride With triethylamine In methanol at 20 - 25℃; for 1h; Stage #2: With hydrogen; 5 % platinum on carbon In methanol at 20 - 35℃; under 750.075 - 3750.38 Torr; for 5h; Product distribution / selectivity;	90%
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 30℃; for 0.166667h; Stage #2: 4-(3-fluoro-benzyloxy)-benzaldehyde In methanol at 30℃; for 3.5h; Stage #3: With sodium hydroxide; sodium tetrahydroborate In methanol; water at 5℃; for 2h; Product distribution / selectivity;	88.5%

4-((2-fluorobenzyl)oxy)benzaldehyde (70627-20-2) + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-[4-(2-fluorobenzyloxy)benzylideneamino]propanamide (1000370-32-0)

Conditions	Yield
With triethylamine In methanol at 20℃; for 1h;	90%

3-((2,3-dihydrobenzo[b][1,4]dioxin-5-oxy)methyl)benzaldehyde + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-(3-((2,3-dihydrobenzo[b][1,4]dioxin-5-oxy)methyl)benzylamino)propionamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 0.5h; Stage #2: 3-((2,3-dihydrobenzo[b][1,4]dioxin-5-oxy)methyl)benzaldehyde In methanol at 20℃; for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	88.83%

3-((2,3-dihydrobenzo[b]thiophen-7-oxy)methyl)benzaldehyde + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-(3-((2,3-dihydrobenzo[b]thiophen-7-oxy)methyl)benzylamino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 0.5h; Stage #2: 3-((2,3-dihydrobenzo[b]thiophen-7-oxy)methyl)benzaldehyde In methanol at 20℃; for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	88.65%

4-((2,3-dihydrobenzofuran-5-oxy)methyl)benzaldehyde + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-(4-((2,3-dihydrobenzofuran-5-oxy)methyl)benzylamino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 0.5h; Stage #2: 4-((2,3-dihydrobenzofuran-5-oxy)methyl)benzaldehyde In methanol at 20℃; for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	88.31%

4-((1H-benzo[d]imidazole-4-oxy)methyl)benzaldehyde + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-((4-(((1H-benzo[d]imidazol-4-yl)oxy)methyl)benzyl)amino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 0.5h; Stage #2: 4-((1H-benzo[d]imidazole-4-oxy)methyl)benzaldehyde In methanol at 20℃; for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	88.06%
Stage #1: (S)-alaninamide hydrochloride With triethylamine In methanol at 20℃; for 1h; Stage #2: 4-((1H-benzo[d]imidazole-4-oxy)methyl)benzaldehyde In methanol for 2h; Stage #3: With potassium borohydride In methanol for 3h; Reflux;	88%

(S)-alaninamide hydrochloride (33208-99-0) + N-(benzyloxycarbonyl)-L-phenylalanine benzyl ester (60379-01-3) → N-(benzyloxycarbonyl)phenylalanyl-alanine amide (65118-54-9)

Conditions	Yield
With S166C-SCH2CH2NH3+; triethylamine; calcium chloride In water; N,N-dimethyl-formamide Ambient temperature;	88%
With triethylamine; wild-type serine protease subtilisin Bacillus lentus In water; N,N-dimethyl-formamide at 20℃; for 24h; pH=5.8;	57%

benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate (7622-21-1) + (S)-alaninamide hydrochloride (33208-99-0) → (S)-N-((S)-1-Carbamoyl-ethyl)-2-hydroxy-3-phenyl-propionamide

Conditions	Yield
With subtilisin bacillus lentus S166C-S-CH2C6F5 mutant enzyme; triethylamine In water; N,N-dimethyl-formamide at 20℃; for 48h;	88%

Upstream product

• 56-41-7 L-alanin 
• 302-72-7 rac-Ala-OH 
• 78981-25-6 tert-butyl (1S)-2-amino-1-methyl-2-oxoethylcarbamate 
• 2491-20-5 L-alanine methyl ester hydrochloride 

Downstream Products

• 141114-44-5 2-<(2,6-dichloro-3-nitrobenzyl)amino>propionamide 
• 50444-54-7 benzyl (S)-1-((S)-1-amino-1-oxopropan-2-ylamino)-1-oxopropan-2-ylcarbamate 
• 1142-20-7 N-Cbz-Ala 
• 449775-52-4 N,N'-(2,2'-dithiobisbenzoyl)-bis-L-alaninamide 
• 74257-69-5 Boc-Phe-Ala-NH₂ 
• 666843-71-6 (S)-2-(2-nitrobenzenesulfonylamino)propionamide 
• 636791-34-9 (S)-N-(1-carbamoyl-ethyl)-2-fluoro-4-(3-fluoro-benzyloxy)-benzamide 
• 1097966-76-1 (1S)-N-[1-carbamoylethyl]-2-phenyl-1H-imidazole-4-carboxamide 
• 1198307-02-6 (S)-N-(1-amino-1-oxopropan-2-yl)-4-octylbenzamide 
• 60756-56-1 (S)-2-amino-N-phenylpropanamide 
• 302911-12-2 BOC-Asp(OBn)-Ala-NH₂ 

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Amino acid amide hydrochloride without inorganic ammonium salt and synthesis method thereof

The present invention discloses an amino acidamide hydrochloride without inorganic ammonium salts and a synthesis method thereof, comprising the following steps: S1, the amino acid under alkaline conditions, added di-tert-butyl dicarbonate to prepare tert-butoxycarbonyl - amino acid; S2, to the prepared tert-butoxycarbonyl - amino acid and then add di-tert-butyl dicarbonate, in the presence of N- methyl morpholine, ammonium bicarbonate, the preparation of tert-butoxycarbonyl - amino acid amide; S3, the tert-butoxycarbonyl - amino acid amide placed in the ethyl acetate / hydrogen chloride solution system, Crystallization is obtained immediately. The present invention is twice added di-tert-butyl dicarbonate, prepared under different conditions to give a high purity tert-butoxycarbonyl - amino acid amide, and finally in the ethyl acetate / hydrogen chloride solution conditions to obtain the final product, the present invention solves the problem of inorganic ammonium salts in the production of amino acid amide hydrochloride difficult to separate, reducing the amount of organic solvent.

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