625-08-1

Basic information

• Product Name: BETA-HYDROXYISOVALERIC ACID
• Synonyms: RARECHEM AL BO 2324;3-B-HYDROXYBUTYRIC ACID;3-HYDROXY-3-METHYLBUTANOIC ACID;3-HYDROXY-3-METHYL BUTYRIC ACID;BETA-HYDROXYISOVALERIC ACID;BETA-HYDROXY-3-METHYL BUTYRIC ACID;BETA-HYDROXY BETA-METHYLBUTYRATE;HYDROXYISOVALERIC ACID, BETA-
• CAS NO: 625-08-1
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.13
• EINECS: 1592732-453-0
• Product Categories: Pharmaceutical Raw Materials;Diagnostic;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Diagnostic, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 625-08-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: −80 °C(lit.)
• Boiling Point: 88 °C1 mm Hg(lit.)
• Flash Point: 113 °C
• Appearance: Pale yellow/Liquid
• Density: 0.938 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00567mmHg at 25°C
• Refractive Index: n20/D 1.4415(lit.)
• Storage Temp.: Refrigerator
• PKA: 4.38±0.10(Predicted)
• Water Solubility: Soluble in water and ethanol.
• BRN: 1743952
• CAS DataBase Reference: BETA-HYDROXYISOVALERIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-HYDROXYISOVALERIC ACID(625-08-1)
• EPA Substance Registry System: BETA-HYDROXYISOVALERIC ACID(625-08-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• WGK Germany: 3
• F: 10-13-21
• Hazardous Substances Data: 625-08-1(Hazardous Substances Data)

Usage

Description

BETA-HYDROXYISOVALERIC ACID, also known as β-Hydroxy β-methylbutyric acid (HMB) or β-hydroxy β-methylbutyrate, is a metabolite of the essential amino acid leucine and is synthesized in the human body. It plays a part in protein synthesis and has been studied for its potential effects on increasing muscle mass and decreasing muscle breakdown.

Uses

Used in Sports Nutrition:
BETA-HYDROXYISOVALERIC ACID is used as a supplement for enhancing muscle growth and strength. It is particularly beneficial for untrained individuals and has been shown to increase muscle mass and decrease body fat in elderly men.
Used in Medical Applications:
BETA-HYDROXYISOVALERIC ACID is used as a treatment for various conditions involving muscle wasting, such as chronic obstructive pulmonary disease, HIV or AIDS, cancer, and severe injuries in trauma victims.
Used in Research:
BETA-HYDROXYISOVALERIC ACID is used as a biochemical for synthesis and proteomics research, as well as an indicator of biotin deficiency.
Used in the Pharmaceutical Industry:
BETA-HYDROXYISOVALERIC ACID is used as a precursor in the synthesis of various pharmaceutical compounds.
Chemical Properties:
BETA-HYDROXYISOVALERIC ACID is a colorless to light yellow liquid.

InChI:InChI=1/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)

Synthetic route

ethyl 3-hydroxy-3-methylbutanoate (18267-36-2) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With water; sodium hydroxide at 20℃;	93%
With sodium hydroxide In water at 20℃;	93%

6,6-dimethyl-4-oxo-2-phenyl-[1,3]oxazinane-3-carboxylic acid tert-butyl ester → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With lithium hydroxide; water In ethanol at 20℃; for 3h; Hydrolysis;	91%

C11H16NO2(1+)*I(1-) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
Stage #1: C11H16NO2(1+)*I(1-) With sodium hydroxide In water at 90℃; for 1h; Stage #2: With hydrogenchloride In water	54%

C11H16NO2(1+)*Cl(1-) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
Stage #1: C11H16NO2(1+)*Cl(1-) With sodium hydroxide In water at 90℃; for 1h; Stage #2: With hydrogenchloride In water	41%

3-hydroxy-3-methylbutyronitrile (13635-04-6) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With water In aq. phosphate buffer at 37℃; for 24h; Reagent/catalyst; Enzymatic reaction;	26%

4,4-dimethyloxetan-2-one (1823-52-5) → 3-Hydroxy-3-methylbutyric acid (625-08-1) + isobutene (115-11-7)

Conditions	Yield
With water

3-methylbutyric acid (503-74-2) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With alkaline permanganate

2-methylpent-4-en-2-ol (624-97-5) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With permanganate(VII) ion
With chromic acid

chloroform (67-66-3) + 5-acetoxy-5-methyl-hex-1-en-3-one (873380-25-7) → formic acid (64-18-6) + 3-Hydroxy-3-methylbutyric acid (625-08-1) + acetic acid (64-19-7)

Conditions	Yield
beim Ozonisieren und Zersetzen des Ozonids mit H2O2;

(±)-4-methyl-1,2,4-pentanetriol (871888-50-5) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With permanganate(VII) ion

4-Hydroxy-4-methyl-2-pentanone (123-42-2) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With sodium hypobromide
With 1,4-dioxane; alkaline aqueous sodium hypochlorite
With sodium hypochlorite

4-hydroxy-6-methyl-heptanoic acid → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With permanganate(VII) ion in alkalischer Loesung;

tert-butyl 3-hydroxy-3-methylbutyrate (5292-12-6) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With 1,4-dioxane; hydrogenchloride

ethyl acetate (141-78-6) + acetone (67-64-1) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With potassium hydroxide; diethyl ether

chloroacetic acid ethyl ester (105-39-5) + acetone (67-64-1) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With zinc Zersetzen des Reaktionsprodukts mit verduennter Schwefelsaeure und Verseifen des entstehenden Aethylesters mit waessr.Kalilauge;

acetone (67-64-1) + ethyl iodoacetae (623-48-3) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With zinc Zersetzen des Reaktionsprodukts mit verduennter Schwefelsaeure und Verseifen des entstehenden Aethylesters mit waessr.Kalilauge;

4-hydroxy-4-methyl-2-oxo-pentanal (10435-98-0) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With dihydrogen peroxide

bromoacetic acid tert-butyl ester (5292-43-3) + acetone (67-64-1) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
(i) Zn, I2, (ii) (hydrolysis); Multistep reaction;

lithium α-lithioacetate (94953-76-1) + acetone (67-64-1) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

2-methyl-1-buten-4-ol (763-32-6) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With nitric acid; sodium nitrite 1) 20 deg C, 4 h, 2) 50-60 deg C, 4 h; Yield given. Multistep reaction;

4-methyl-2-oxopentanoic acid (816-66-0) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
With oxygen; iron(III); ascorbic acid; diothiothreitol

4-isobutyl-γ-butyrolactone (18432-37-6) + KOH-solution + potassium permanganate → 3-Hydroxy-3-methylbutyric acid (625-08-1)

4,4-dimethyloxetan-2-one (1823-52-5) + water (7732-18-5) → 3-Hydroxy-3-methylbutyric acid (625-08-1) + isobutene (115-11-7)

diethyl ether (60-29-7) + ethyl acetate (141-78-6) + acetone (67-64-1) + KOH → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
anfangs unter Eiskuehlung und Verseifen mit alkoh. KOH;

3-methyl-butane-1,3-diol (2568-33-4) + KMnO4 → 3-Hydroxy-3-methylbutyric acid (625-08-1)

2-methylpent-4-en-2-ol (624-97-5) + chamaeleon solution → formic acid (64-18-6) + 3-Hydroxy-3-methylbutyric acid (625-08-1) + oxalic acid (144-62-7)

2-methylpent-4-en-2-ol (624-97-5) + chromic acid solution → formic acid (64-18-6) + 3-Hydroxy-3-methylbutyric acid (625-08-1) + acetone (67-64-1)

perchloric acid (7601-90-3) + 3-Methylbutenoic acid (541-47-9) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
at 82.4℃; Kinetics;
at 99.8℃; Kinetics;
at 111.8℃; Kinetics;

3-Methylbutenoic acid (541-47-9) + aqueous NaClO4 → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Conditions	Yield
at 82.4℃; Kinetics;
at 99.8℃; Kinetics;
at 111.8℃; Kinetics;

ethyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-1-thio-β-D-glucopyranoside (861819-35-4) + 3-Hydroxy-3-methylbutyric acid (625-08-1) → ethyl 3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-1-thio-β-D-glucopyranoside (861819-36-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1h;	100%

3-Hydroxy-3-methylbutyric acid (625-08-1) + 3,5-dimethylaminoaniline (108-69-0) → C13H19NO2

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 14h;	100%

3-Hydroxy-3-methylbutyric acid (625-08-1) + 4-bromodeacetyl colchicine → 4-bromo-N-(3-hydroxy-3-methylbutyryl)deacetyl colchicine

Conditions	Yield
Stage #1: 3-Hydroxy-3-methylbutyric acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4-bromodeacetyl colchicine In N,N-dimethyl-formamide at 20℃;	98.4%

3-Hydroxy-3-methylbutyric acid (625-08-1) + (R)-benzyl 2-aminopropanoate hydrochloride (5557-81-3, 5557-83-5, 34404-37-0) → (R)-benzyl 2-(3-hydroxy-3-methylbutanamido)propanoate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0 - 20℃; for 1h;	98%

3-Hydroxy-3-methylbutyric acid (625-08-1) + 4-(6-(4,7-diazaspiro[2.5]octan-7-yl)pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride → 4-(6-(4-(3-hydroxy-3-methylbutanoyl)-4,7-diazaspiro[2.5]octan-7-yl)pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions	Yield
With 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h;	98%

3-Hydroxy-3-methylbutyric acid (625-08-1) + 2-methoxy-phenylamine (90-04-0) → C12H17NO3

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 14h;	98%

5-methoxycarbonylpentyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside + 3-Hydroxy-3-methylbutyric acid (625-08-1) → 5-methoxycarbonylpentyl 3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutyramido)-2-O-methyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Conditions	Yield
With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1h;	97%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1h;	97%

3-Hydroxy-3-methylbutyric acid (625-08-1) + C89H71F102N9O8 → C94H79F102N9O10

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	96%

3-Hydroxy-3-methylbutyric acid (625-08-1) + Ν,Ν',Ν''-[boroxin-2,4,6-triyltris[[(1R)-3-methylbutane-1,1-diyl]imino(2-oxoethane-2,1-diyl)]]tris(2,5-dichlorobenzamide) (1201903-03-8) → 2,5-dichloro-N-(2-{[(1R)-1-(4,4-dimethyl-6-oxo-1,3,2-dioxaborinan-2-yl)-3-methylbutyl]amino}-2-oxoethyl)benzamide (1201902-88-6)

Conditions	Yield
In ethyl acetate at 25 - 60℃;	95%

3-Hydroxy-3-methylbutyric acid (625-08-1) + C45H69NO17 (1040140-55-3) → C50H77NO19 (1040140-56-4)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In tetrahydrofuran for 10h;	92%

5-methoxycarbonylpentyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside + 3-Hydroxy-3-methylbutyric acid (625-08-1) → 5-methoxycarbonylpentyl 3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutyramido)-2-O-methyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h;	90%

5-(4-(4-(5-amino-4-(benzyloxy)tetrahydro-3-methoxy-6-methyl-2H-pyran-2-yloxy)tetrahydro-3,5-dihydroxy-6-methyl-2H-pyran-2-yloxy)-3,5-dihydroxytetrahydro-6-methyl-2H-pyran-2-yloxy)-6-(benzyloxy)tetrahydro-2-methyl-2H-pyran-3,4-diol + 3-Hydroxy-3-methylbutyric acid (625-08-1) → C44H65O18N

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In tetrahydrofuran for 10h;	90%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In tetrahydrofuran for 10h;	90%

3-Hydroxy-3-methylbutyric acid (625-08-1) + (3aR,6aR)-5-[1-(2-fluorophenyl)-1H-indazol-4-yl]hexahydropyrrolo[3,4-b]pyrrol-6(1H)-one → (3aR,6aR)-5-[1-(2-fluorophenyl)-1H-indazol-4-yl]-1-(3-hydroxy-3-methylbutanoyl)hexahydropyrrolo[3,4-b]pyrrol-6-(1H)-one

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile for 2h;	90%

3-Hydroxy-3-methylbutyric acid (625-08-1) + m-Anisidine (536-90-3) → C12H17NO3

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 14h;	90%

C81H99NO18 + 3-Hydroxy-3-methylbutyric acid (625-08-1) → C86H107NO20

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1h;	89%
With diazoacetic acid ethyl ester; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane	73%

5-methoxycarbonylpentyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside + 3-Hydroxy-3-methylbutyric acid (625-08-1) → 5-methoxycarbonylpentyl 3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutyramido)-2-O-methyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h;	86%

3-Hydroxy-3-methylbutyric acid (625-08-1) + methyl 4-amino-4,6-dideoxy-2-O-methyl-β-D-glucopyranoside → methyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranoside

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.333333h;	85%

3-Hydroxy-3-methylbutyric acid (625-08-1) + methyl 3-O-(4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-2,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (1149356-84-2) → methyl 2,4-di-O-benzyl-3-O-[3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-β-D-glucopyranosyl]-1-thio-α-L-rhamnopyranoside (1149356-85-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 1.5h;	85%

3-Hydroxy-3-methylbutyric acid (625-08-1) → 1-Amino-2-methyl-propan-2-ol (2854-16-2)

Conditions	Yield
Stage #1: 3-Hydroxy-3-methylbutyric acid With 4-methyl-morpholine; diphenyl phosphoryl azide In tetrahydrofuran at 25℃; for 2.25h; Curtius Rearrangement; Stage #2: With water In tetrahydrofuran for 2h; Reagent/catalyst; Reflux;	85%

3-Hydroxy-3-methylbutyric acid (625-08-1) + aniline (62-53-3) → β-hydroxy-isovaleric acid anilide (99985-75-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 14h;	85%

3-Hydroxy-3-methylbutyric acid (625-08-1) + C65H70N2O18 → N-benzyloxycarbonylaminoethyl 4-(3-hydroxy-3-methylbutamido)-2-O-acetyl-3-O-benzoyl-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-D-rhamnopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-D-rhamnopyranoside (1206451-89-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 18h; Inert atmosphere;	82%

ethanol (64-17-5) + 3-Hydroxy-3-methylbutyric acid (625-08-1) → ethyl 3-hydroxy-3-methylbutanoate (18267-36-2)

Conditions	Yield
With toluene-4-sulfonic acid In cyclohexane at 85℃; for 5h; Reagent/catalyst; Solvent; Molecular sieve;	80%

3-Hydroxy-3-methylbutyric acid (625-08-1) + 6-(1-methyl-1H-pyrazol-4-yl)-4-(6-(piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile → 4-(6-(4-(3-hydroxy-3-methylbutanoyl)piperazin-1-yl)pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	80%

3-Hydroxy-3-methylbutyric acid (625-08-1) + methyl 4-amino-4,6-dideoxy-2-O-methyl-α-D-glucopyranoside (861819-29-6) → methyl 4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-α-D-glucopyranoside

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.5h;	79%

C64H72N2O16 + 3-Hydroxy-3-methylbutyric acid (625-08-1) → 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (927680-52-2)

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h;	78%

5-methoxycarbonylpentyl 4-amino-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-β-D-glucopyranosyl-(1->2)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside + 3-Hydroxy-3-methylbutyric acid (625-08-1) → 5-methoxycarbonylpentyl 2-O-benzoyl-3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutyramino)-β-D-glucopyranosyl-(1->2)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h;	78%

5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride + 3-Hydroxy-3-methylbutyric acid (625-08-1) → TAK-285

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 72h;	77%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 120h;

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 3-Hydroxy-3-methylbutyric acid (625-08-1) → β-hydroxyisovaleric acid succinimidyl ester (1314864-92-0)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	77%

Upstream product

• 1823-52-5 4,4-dimethyloxetan-2-one 
• 503-74-2 3-methylbutyric acid 
• 624-97-5 2-methylpent-4-en-2-ol 
• 67-66-3 chloroform 
• 873380-25-7 5-acetoxy-5-methyl-hex-1-en-3-one 
• 871888-50-5 (±)-4-methyl-1,2,4-pentanetriol 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 5292-12-6 tert-butyl 3-hydroxy-3-methylbutyrate 
• 141-78-6 ethyl acetate 
• 67-64-1 acetone 
• 105-39-5 chloroacetic acid ethyl ester 
• 623-48-3 ethyl iodoacetae 
• 10435-98-0 4-hydroxy-4-methyl-2-oxo-pentanal 
• 5292-43-3 bromoacetic acid tert-butyl ester 

Downstream Products

• 541-47-9 3-Methylbutenoic acid 
• 75-65-0 tert-butyl alcohol 
• 861819-36-5 ethyl 3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-1-thio-β-D-glucopyranoside 
• 927680-51-1 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 927680-52-2 3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 84474-35-1 3'-Hydroxy T-2 toxin 
• 97373-17-6 3'-Hydroxy HT-2 toxin 
• 629948-76-1 (2R,4S)-1-{N-(3,5-bistrifluoromethylbenzyl)-N-methyl}aminocarbonyl-2-(4-fluoro-2-methylphenyl)-4-{1-(3-hydroxy-3-methylbutyryl)piperidine-4-yl}aminocarbonyloxypiperidine 
• 37526-90-2 benzyl 3-hydroxy-3-methylbutyrate 

Relevant articles and documents

PROCESS FOR PREPARING 3-HYDROXY-3-METHYLBUTYRATE (HMB) AND SALTS THEREOF

The present invention pertains to a process for preparing 3-hydroxy-3-methylbutyrate (HMB) or a salt thereof, the method comprising (a) reacting isobutylene oxide with cyanide in order to obtain 3- hydroxy-3-methylbutyronitrile, and (b) hydrolyzing the 3-hydroxy-3-methylbutyronitrile obtained in step (a) in order to obtain HMB, wherein hydrolysis step (b) is performed using either at least one nitrilase enzyme or, alternatively, using a combination of enzymes, said combination comprising at least one nitrile hydratase and at least one amidase.

Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound

Provided are: a method for producing an aliphatic carboxylic acid compound safely and easily from a starting material that can be obtained or produced industrially without generating a harmful substance such as haloform; and a pyridine compound adduct of an aliphatic ketone compound. The method for producing an aliphatic carboxylic acid compound is a method for producing an aliphatic carboxylic acid compound represented by Formula (I), and comprises: a first step for obtaining a pyridine compound adduct by adding a pyridine compound to an aliphatic ketone compound having an alpha-methyl groupin the presence of an oxidizing agent; and a second step of hydrolyzing the pyridine compound adduct in the presence of a base. In the Formula, R1 represents a substituted or unsubstituted linear alkyl group having 4-8 carbon atoms or a substituted or unsubstituted branched alkyl group having 4-8 carbon atoms; M represents hydrogen, a metal belonging to Group 1 or Group 2 of the periodic table, amethyl group, an ethyl group, an n-propyl group or an isopropyl group.

Substituted heteroaryl compounds and compositions and uses thereof (by machine translation)

The invention discloses substituted heteroaryl compounds and compositions thereof and their use. The compounds of formula (I) compound or type shown in (I) a compound represented by stereo isomers, tautomers, nitrogen oxide, solvate, metabolite, pharmaceutically acceptable salt or its prodrug. The invention also provides a pharmaceutical composition, the compounds and pharmaceutical compositions can be regulated protein kinase, particularly Aurora kinase and JAK kinase activity, for the prevention, treatment, treatment and reduce protein kinase, in particular JAK kinase activity mediated diseases or disorders. (by machine translation)