625-08-1

Usage

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 
• 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 
• 871026-44-7 TAK-285 

Relevant academic research and scientific papers

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.

Preparation method of calcium [beta]-hydroxy-[beta]-methylbutyrate

The invention discloses a preparation method of calcium [beta]-hydroxy-[beta]-methylbutyrate, which comprises the following steps: S1) condensation reaction: adding ethyl chloroacetate and acetone into a solvent, and dropwisely adding an alkali solution to obtain a 3, 3-dimethyl oxide-2-carboxylic acid ethyl ester solution; S2) hydrolysis reaction: adding an aqueous solution of alkali into a solution of 3, 3-dimethyl oxide-2-carboxylic acid ethyl ester, and performing acidifying to obtain 3, 3-dimethyl oxide-2-carboxylic acid; S3) hydrogenation reaction: adding 3, 3-dimethyl oxide-2-carboxylicacid into the Pt/C alcohol system, and performing hydrogenation to obtain [beta]-hydroxy-[beta]-methylbutyrate acid; and S4) salifying reaction: adding water, calcium salt and a catalyst into the organic solution of [beta]-hydroxy-[beta]-methylbutyrate acid to react, and performing filtering, pulping and drying to prepare the finished product calcium [beta]-hydroxy-[beta]-methylbutyrate. The preparation method disclosed by the invention is simple in process, easy to operate, environment-friendly, free of pollution, safe in calcium reagent, free of residue, low in cost, safe to operate, easy for industrial large-scale production, high in conversion rate and good in product quality.

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.

SUBSTITUTED HETEROARYL COMPOUNDS AND METHODS OF USE

The present invention provides novel heteroaryl compounds, pharmaceutical acceptable salts and formulations thereof. They are useful in preventing, managing, treating or lessening the severity of a protein kinase-mediated disease. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of protein kinase-mediated disease.

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)

HMB-Ca production process method

The invention discloses HMB-Ca production process method, which comprises the following steps that HMB is dissolved in water; calcium salt is added; stirring, filtering and concentration are performedto obtain an HMB-Ca crude product; the HMB-Ca crude product is added into an alcohol solvent; after stirring, filtering and concentration are performed, an organic solvent is added; stirring and filtering are performed; solid drying is performed to obtain an HMB-Ca product; during the filtering, the hole diameter is 1 to 100 micrometers. The HMB-Ca production process method has the advantages that the production operation and purification filtering conditions of the HMB-Ca product are optimized; the mechanical impurities and the metal ion residues in the HMB-Ca product are effectively reduced; the safety when the HMB-Ca product is used as a health care product and food additive is improved; the process conditions are mild; the operation is easy; the production operation safety degrade isreduced; green and environment-friendly effects are achieved; the industrialization is favorably realized.

Beta-HYDROXY-Beta-METHYLBUTYRIC ACID PURIFICATION METHOD

The present invention relates to a method for purifying β-hydroxyl-β-methyl butyrate, comprising neutralizing a crude β-hydroxyl-β-methyl butyrate with a base to produce a salt of β-hydroxyl-β-methyl butyrate, cooling and crystallizing, dissolving and acidifying, and extracting to obtain β-hydroxyl-β-methyl butyrate of high purity. No strict conditions, such as high temperature and high vacuum, are required in this method. On the contrary, it has low requirement on the apparatus, the process can readily be controlled and a product with high purity can be produced.

METHODS FOR PRODUCING 3-HYDROXY-3-METHYLBUTYRIC ACID

Described is a method for the conversion of 3-methylcrotonyl-CoA into 3-hydroxy-3- methylbutyric acid comprising the steps of: (a) enzymatically converting 3-methylcrotonyl-CoA into 3-hydroxy-3-methylbutyryl-CoA; and (b) further enzymatically converting the thus produced 3-hydroxy-3-methylbutyryl-CoA into 3-hydroxy-3-methylbutyric acid wherein the enzymatic conversion of 3-hydroxy-3-methylbutyryl-CoA into 3-hydroxy-3-methylbutyric acid according to step (b) is achieved by first converting 3-hydroxy-3-methylbutyryl-CoA into 3-hydroxy-3-methylbutyryl phosphate and then subsequently converting the thus produced 3-hydroxy-3-methylbutyryl phosphate into 3-hydroxy-3-methylbutyric acid.

Method for the enzymatic production of 3-hydroxy-3-methylbutyric acid from acetone and acetyl-CoA

Described is a method for the production of 3-hydroxy-3-methylbutyric acid (also referred to as beta-hydroxyisovalerate or HIV) from acetone and a compound which provides an activated acetyl group comprising the enzymatic conversion of acetone and a compound which provides an activated acetyl group into 3-hydroxy-3-methylbutyric acid. The conversion makes use of an enzyme which is capable of catalyzing the formation of a covalent bond between the carbon atom of the oxo (i.e. the C=O) group of acetone and the methyl group of the compound which provides an activated acetyl group. Preferably, the enzyme employed in the process is an enzyme with the activity of a HMG CoA synthase (EC 2.3.3.10) and/or a PksG protein and/or an enzyme with the activity of a C-C bond cleavage/condensation lyase, such as a HMG CoA lyase (EC 4.1.3.4). Also described are organisms which are able to produce 3-hydroxy-3-methylbutyric acid from acetone, a compound which provides an activated acetyl group, the use of the above-mentioned enzymes and organisms for the production of 3-hydroxy-3-methylbutyric acid as well as the use of acetone for the production of 3-hydroxy-3-methylbutyric acid.

Gold(I)/copper(II)-cocatalyzed tandem cyclization/semipinacol reaction: Construction of 6-Aza/Oxa-Spiro[4.5]decane skeletons and formal synthesis of (±)-halichlorine

A simple and efficient strategy for the construction of 6-aza/oxa-spiro[4.5]decane skeletons under the cocatalysis of gold(I)/copper(II) was developed, and its potential utility was demonstrated by a formal synthesis of the biologically active marine alkaloid (±)-halichlorine.