63038-27-7

Basic information

• Product Name: L-TERT-LEUCINE METHYL ESTER HYDROCHLORIDE
• Synonyms: (S)-2-AMINO-3,3-DIMETHYLBUTYRIC ACID METHYL ESTER HYDROCHLORIDE;L-(+)-TERT-LEUCINE METHYL ESTER HYDROCHLORIDE;L-TERT-LEUCINE METHYL ESTER HYDROCHLORIDE;L-(+)-METHYL TERT-LEUCINATE HYDROCHLORIDE;METHYL (S)-2-AMINO-3,3-DIMETHYLBUTYRATE HYDROCHLORIDE;L-(+)-methyl-tert-leucinateHCl;METHYL L-2-AMINO-3,3-DIMETHYLBUTANOATE HYDROCHLORIDE;(S)-methyl 2-amino-3,3-dimethylbutanoate hydrochloride
• CAS NO: 63038-27-7
• Molecular Formula: C₇H₁₆NO₂*Cl
• Molecular Weight: 181.66
• EINECS: 1312995-182-4
• Product Categories: API intermediates;Amino Acid Methyl Esters;Amino Acids;Amino Acids (C-Protected);Biochemistry;Leucine Derivatives;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 63038-27-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 183-186 °C
• Boiling Point: 206.8 °C at 760 mmHg
• Flash Point: 78.9 °C
• Appearance: /
• Vapor Pressure: 0.195mmHg at 25°C
• Refractive Index: 16.5 ° (C=1, MeOH)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• BRN: 4879785
• CAS DataBase Reference: L-TERT-LEUCINE METHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-TERT-LEUCINE METHYL ESTER HYDROCHLORIDE(63038-27-7)
• EPA Substance Registry System: L-TERT-LEUCINE METHYL ESTER HYDROCHLORIDE(63038-27-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 63038-27-7(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

L-tert-Leucine Methyl Ester Hydrochloride is used in the preparation of peptidomimetic protease inhibitors.

InChI:InChI=1/C7H15NO2.ClH/c1-7(2,3)5(8)6(9)10-4;/h5H,8H2,1-4H3;1H/t5-;/m1./s1

Synthetic route

methanol (67-56-1) + L-tert-Leucine (20859-02-3) → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
With thionyl chloride at 0 - 20℃;	100%
With thionyl chloride for 16h; Reflux;	100%
With hydrogenchloride Ambient temperature;	98%

methanol (67-56-1) + N-tert-butyloxycarbonyl-L-tert-leucine (62965-35-9) → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
With thionyl chloride at 0 - 80℃; for 8h; Inert atmosphere;	76%
With thionyl chloride at 80℃; for 8h;	76%
With thionyl chloride at 20℃; Cooling;

methanol (67-56-1) + t-butoxycarbonyl-L-t-butylglycine dicyclohexylamine salt → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
With thionyl chloride at 40℃;	52%

L-tert-Leucine (20859-02-3) → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 2: 52 percent / SOCl2 / 40 °C View Scheme

2-<(S)-α-methylbenzylamino>-3,3,dimethylbutyramide (75158-11-1) → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / hydrogen / 10percent Pd/C / acetic acid; methanol / 760 Torr / Ambient temperature 2: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C 3: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 4: 52 percent / SOCl2 / 40 °C View Scheme

pivalaldehyde (630-19-3) → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
Multi-step reaction with 7 steps 1: diethyl ether / -10 °C 2: 75 percent / ethanol 3: 81 percent / H2SO4 4: 80 percent / hydrogen / 10percent Pd/C / acetic acid; methanol / 760 Torr / Ambient temperature 5: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C 6: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 7: 52 percent / SOCl2 / 40 °C View Scheme

1-<(S)-α-methylbenzylimino>-2,2-dimethylpropane (33978-37-9) → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
Multi-step reaction with 6 steps 1: 75 percent / ethanol 2: 81 percent / H2SO4 3: 80 percent / hydrogen / 10percent Pd/C / acetic acid; methanol / 760 Torr / Ambient temperature 4: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C 5: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 6: 52 percent / SOCl2 / 40 °C View Scheme

2-<(S)-α-methylbenzylamino>-3,3-dimethylbutyronitrile → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 81 percent / H2SO4 2: 80 percent / hydrogen / 10percent Pd/C / acetic acid; methanol / 760 Torr / Ambient temperature 3: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C 4: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 5: 52 percent / SOCl2 / 40 °C View Scheme

(S)-2-amino-3,3-dimethylbutanamide hydrochloride → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C 2: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 3: 52 percent / SOCl2 / 40 °C View Scheme

methanol (67-56-1) + (S)-2-amino-3,3-dimethylbutanoic acid hydrochloride (139163-43-2) → L-tert-leucine methyl ester hydrochloride (63038-27-7)

Conditions	Yield
With thionyl chloride at -10 - 20℃; for 16h;

L-tert-leucine methyl ester hydrochloride (63038-27-7) + 4-Nitrophenyl chloroformate (7693-46-1) → methyl (2S)-3,3-dimethyl-2-{[(4-nitrophenoxy)carbonyl]amino}butanoate (854755-78-5)

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at 25℃; for 64h;	100%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + chloroacetyl chloride (79-04-9) → methyl (2S)-2-[(chloroacetyl)amino]-3,3-dimethylbutanoate (854746-00-2)

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 25℃; for 4h;	100%

(R)-3-benzyloxycarbonyl-2-pentylpropanoic acid (611212-55-6) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → N-[(R)-3-benzyloxycarbonyl-2-pentylpropanoyl]-L-tert-leucine methyl ester (1035610-03-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	100%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + acetone (67-64-1) → methyl (S)-2-(isopropylamino)-3,3-dimethylbutanoate hydrochloride (1312680-06-0)

Conditions	Yield
With 4-methyl-morpholine; palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 3000.3 Torr; for 12h; Inert atmosphere; chemoselective reaction;	100%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + trifluoroacetic anhydride (407-25-0) → C9H14F3NO3

Conditions	Yield
With triethylamine In dichloromethane at -78℃; for 3h; Inert atmosphere;	100%

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → Boc-Ser-Tle-OMe

Conditions	Yield
Stage #1: L-tert-leucine methyl ester hydrochloride With sodium carbonate In dichloromethane; water at 20℃; for 0.0833333h; Stage #2: (S)-N-(tert-butoxycarbonyl)serine With C12H6B2Br4O3 In 1,2-dichloro-ethane at 90℃; for 24h; chemoselective reaction;	97%

sodium tetrachloropalladate(II) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → trans-[methyl-(L)-tert-leucinate]2PdCl2

Conditions	Yield
With sodium acetate In water under Ar or N2, Pd-complex was added to mixt. of 2 equiv. of amino-acidand 2 equiv. of NaOOCCH3, 1 h; ppt. was filtered off, dried in high vac.;	90%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + Propiolic acid (471-25-0) → C10H15NO3 (1259216-71-1)

Conditions	Yield
Stage #1: L-tert-leucine methyl ester hydrochloride; Propiolic acid With N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 0 - 23℃; for 16.16h; Inert atmosphere; Stage #2: With water; ammonium chloride In dichloromethane	90%

N-(tert-butoxycarbonyl)-N-methyl-L-alanine (16948-16-6) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoate (876623-92-6)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 20℃; for 18h;	90%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + 5-acetyl-2,2-dimethyl-1,3-dioxane-4,6-dione (72324-39-1) → methyl 3,3-dimethyl-2-(3-oxobutanamido)butanoate

Conditions	Yield
With triethylamine In 1,4-dioxane at 110℃; for 4h;	88%

1-(5-fluoro-4-hydroxypentyl)-1H-indole-3-carboxylic acid + L-tert-leucine methyl ester hydrochloride (63038-27-7) → methyl (2S)-2-(1-(5-fluoro-4-hydroxypentyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate

Conditions	Yield
Stage #1: 1-(5-fluoro-4-hydroxypentyl)-1H-indole-3-carboxylic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In acetonitrile at 20℃; for 0.5h; Stage #2: L-tert-leucine methyl ester hydrochloride In acetonitrile at 20℃; for 48h;	87%

9H-fluoren-9-ylmethyl (1-methyl-1H-benzimidazol-2-yl)methyl(2-oxoethyl)carbamate (854745-42-9) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → tert-butyl (2S)-2-[(2-{[(9H-fluoren-9-ylmethoxy)carbonyl][(1-methyl-1H-benzimidazol-2-yl)methyl]amino}ethyl)amino]-3,3-dimethylbutanoate (854755-70-7)

Conditions	Yield
Stage #1: 9H-fluoren-9-ylmethyl (1-methyl-1H-benzimidazol-2-yl)methyl(2-oxoethyl)carbamate; L-tert-leucine methyl ester hydrochloride With sodium cyanoborohydride; acetic acid In methanol at 25℃; for 3.5h; Stage #2: With water In methanol; ethyl acetate	83%

9H-fluoren-9-ylmethyl (1-methyl-1H-benzimidazol-2-yl)methyl(2-oxoethyl)carbamate (854745-42-9) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → Methyl (2S)-2-[(2-{[(9H-fluoren-9-ylmethoxy)carbonyl][(1-methyl-1H-benzimidazol-2-yl)methyl]amino}ethyl)amino]-3,3-dimethylbutanoate (854745-43-0)

Conditions	Yield
With sodium cyanoborohydride In methanol; acetic acid at 25℃; for 3.5h;	83%
With sodium cyanoborohydride; acetic acid In methanol at 25℃; for 3.5h;	83%
With sodium cyanoborohydride; acetic acid In methanol at 25℃; for 3.5h;	83%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → (2S)-tert-butyl 2S-((2S)-1-(methoxycarbonyl)-2,2-dimethylpropylcarbamoyl)pyrrolidine-1-carboxylate (125769-55-3)

Conditions	Yield
Stage #1: 1-(tert-butoxycarbonyl)-L-proline; L-tert-leucine methyl ester hydrochloride With triethylamine In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 17h;	82.2%
Stage #1: 1-(tert-butoxycarbonyl)-L-proline In tetrahydrofuran; butan-1-ol at 0℃; for 0.166667h; Stage #2: L-tert-leucine methyl ester hydrochloride With triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran; butan-1-ol at 20℃; for 25h;	58%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + piperic acid (136-72-1) → methyl (S)-2-((2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienamido)-3,3-dimethylbutanoate

Conditions	Yield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h;	82%

4'-(methyloxy)-3-nitro-4-biphenylcarboxylic acid (669002-29-3) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → C21H24N2O6 (887243-26-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	81%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + acryloyl chloride (814-68-6) → (S)-N-1-methoxycarbonyl-1-tert-butylmethyl-acrylamide (904927-42-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	80%

1-pentyl-1H-indazole-3-carboxylic acid + L-tert-leucine methyl ester hydrochloride (63038-27-7) → MDMB-PINACA

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 0 - 20℃; for 2h;	76%

(2E,4E)-4-(benzo[d][1,3]dioxol-5-ylmethylene)hex-2-enoic acid (911410-81-6) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → methyl (S)-2-((2E,4E)-4-(benzo[d][1,3]dioxol-5-ylmethylene)hex-2-enamido)-3,3-dimethylbutanoate

Conditions	Yield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h;	75%

phosgene (75-44-5) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → methyl 3-methyl-N-(oxomethylene)-L-valinate (144164-32-9)

Conditions	Yield
With pyridine In dichloromethane; toluene at 0℃; for 1.5h;	74%
With pyridine In dichloromethane; toluene at 0℃; for 2h;

5-Hexen-1-ol (821-41-0) + hex-5-en-1-al (764-59-0) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → methyl N-hex-5-en-1-yl-3-methyl-L-valinate (1000063-68-2)

Conditions	Yield
With triethanolamine; 4,5-dichloro-1-phenylpyridazin-6-one; sodium tris(acetoxy)borohydride	72%

1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid + L-tert-leucine methyl ester hydrochloride (63038-27-7) → methyl (S)-2-(1-(5-fluoropentyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamido)-3,3-dimethylbutanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	72%

8-(tert-butoxycarbonyl)-3-phenyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxylic acid (1094091-87-8) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → (S)-tert-butyl 1-(1-methoxy-3,3-dimethyl-1-oxobutan-2-ylcarbamoyl)-3-phenyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-8(9H)-carboxylate (1094091-88-9)

Conditions	Yield
Stage #1: 8-(tert-butoxycarbonyl)-3-phenyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxylic acid; L-tert-leucine methyl ester hydrochloride With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1.33333h; Stage #2: With water; sodium hydrogencarbonate In N,N-dimethyl-formamide	71%

4-nitronaphthalen-1-yl trifluoromethanesulfonate (212057-67-5) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → methyl (S)-3,3-dimethyl-2-((4-nitronaphthalen-1-yl)amino)butanoate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	71%

Boc-D-Phe-OH (18942-49-9) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → C21H32N2O5

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 24.1667h; Inert atmosphere; Sealed tube;	70%

L-tert-leucine methyl ester hydrochloride (63038-27-7) + Benzoylformic acid (611-73-4) → (S)-3,3-Dimethyl-2-(2-oxo-2-phenyl-acetylamino)-butyric acid methyl ester

Conditions	Yield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane	69%

1-(4-fluorobutyl)-1H-indazole-3-carboxylic acid + L-tert-leucine methyl ester hydrochloride (63038-27-7) → methyl (2S)-2-([1-(4-fluorobutyl)-1H-indazole-3-carbonyl]amino)-3,3-dimethylbutanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	68%

2-(benzyloxy)-5-chlorobenzoic acid (52803-75-5) + L-tert-leucine methyl ester hydrochloride (63038-27-7) → methyl (2S)-2-[[2-(benzyloxy)(5-chlorobenzoyl)amino]-3,3-dimethyl]butanoate (1469996-57-3)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 5 - 20℃; for 16.5h;	67%

Upstream product

• 63038-26-6 methyl (2S)-2-amino-3,3-dimethylbutanoate 
• 63038-10-8 (3S)-3β-Butyl-1,3,4,5-tetrahydroisobenzofuran-1-one 
• 6303-80-6 4-(cyclohexylamino)butan-2-one 
• 63038-00-6 5-aminonaphthalene-1,4-dione 
• 63037-96-7 [(7-hydroxynaphthalen-1-yl)oxy]acetic acid 
• 6303-79-3 Piperazine, 2-pentyl- (7CI,8CI,9CI) 
• 6303-78-2 propyl 2-methyl-3-oxopentanoate 
• 6303-77-1 4-methyloctane-3,5-dione 
• 63037-64-9 4-BroMo-3-iodoaniline 
• 63037-63-8 1-Bromo-2-iodo-4-nitrobenzene 
• 6303-76-0 3,3-dimethylheptane-2,4-dione 
• 6303-75-9 N-PENTYLPYRAZINE 
• 6303-74-8 3-methyl-1-(pyrazin-2-yl)butan-2-one 
• 6303-73-7 1-(pyridin-2-yl)butan-2-one 

Downstream Products

• 6303-82-8 1-phenylhexane-1,5-dione 
• 6303-83-9 ethyl 4-oxo-2-phenylpentanoate 
• 6303-84-0 4,4-dimethyl-1-phenylpentan-2-one 
• 630384-20-2 Cyclopropanamine, 1-(4-iodophenyl)- 
• 63038-44-8 Poly-D-leucine 
• 6303-85-1 2-methyl-5-(propan-2-yl)nonane-4,6-dione 
• 6303-86-2 3-hydroxy-3,4-diphenylcyclohexanone 
• 6303-87-3 2-(1,3-diphenylpropan-2-yl)pyrazine 
• 63038-82-4 (1aR,2S,3R,11bS)-1a,2,3,11b-tetrahydrotetrapheno[10,11-b]oxirene-2,3-diol 
• 63038-83-5 Benz(A)anthracene-8,9-diol-10,11-epoxide, anti 
• 6303-88-4 9-METHYL-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE 
• 6303-89-5 1-(pentylamino)but-3-en-2-yl 4-nitrobenzoate 
• 630390-23-7 Cyclopentanecarboxylic acid, 2-(1-methylethyl)-, (1R,2S)- (9CI) 
• 6303-91-9 3-hydroxy-2-methyl-2,3-diphenylpropanoic acid 

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• 78-84-2  isobutyraldehyde 
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• 37736-82-6  (S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid 
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