MLN-2238 supplier | CasNO.1072833-77-2

Name
(R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acid
EINECS 810-246-8
CAS No. 1072833-77-2
Article Data13
CAS DataBase
Density 1.306 g/cm³
Solubility
Melting Point
Formula C₁₄H₁₉BCl₂N₂O₄
Boiling Point
Molecular Weight 361.033
Flash Point
Transport Information
Appearance Solid powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (R)-1-(2-(2,5-Dichlorobenzamido)acetamido)-3-methylbutylboronic acid;
PSA 98.66000
LogP 2.46780

Synthetic route

: 13061-96-6
dihydroxy-methyl-borane

: (R)-2,5-dichloro-N-(2-((3-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)amino)2-oxoethyl)benzamide

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 20℃;	93%

: 13061-96-6
dihydroxy-methyl-borane

: 1201903-02-7
2,5-dichloro-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexa-hydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
With hydrogenchloride In water; acetone at 20℃; for 40h;	92%

: 1201903-02-7
2,5-dichloro-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexa-hydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide

: 11113-50-1
boric acid

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
With hydrogenchloride In di-isopropyl ether at 20℃; for 5h;	86.5%

: 1201903-02-7
2,5-dichloro-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexa-hydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; hexane; water	76.5%
With hydrogenchloride; Dihydroxy-isobutyl-boran In methanol; hexane at 20℃;	63%

: 29022-11-5
N-(fluoren-9-ylmethoxycarbonyl)glycine

: C23H27BNO5Pol

: 50-79-3
2,5-dichlorobenzoic acid

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
Stage #1: C23H27BNO5Pol With piperidine In N,N-dimethyl-formamide for 0.333333h; 1-glycerol polystyrene resin; Stage #2: N-(fluoren-9-ylmethoxycarbonyl)glycine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 2h; 1-glycerol polystyrene resin; Stage #3: 2,5-dichlorobenzoic acid Further stages;	49%

...Expand

: (R)-2,5-dichloro-N-(2-((3-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)amino)2-oxoethyl)benzamide

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate / 12 h / 120 °C 2: hydrogenchloride; water / ethyl acetate / 0.5 h / 20 °C View Scheme
Stage #1: (R)-2,5-dichloro-N-(2-((3-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)amino)2-oxoethyl)benzamide With boron trichloride In dichloromethane at -78℃; Inert atmosphere; Stage #2: With methanol for 0.166667h;	23.0 mg

: (R)-[N-(2,5-dichlorobenzoyl)glycyl]leucine borate diethanolamine ester

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
With hydrogenchloride; water In ethyl acetate at 20℃; for 0.5h;

: 50-79-3
2,5-dichlorobenzoic acid

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 0.5 h 1.2: 12 h / 20 °C 2.1: lithium hydroxide; water / tetrahydrofuran / 0.5 h / 20 °C 3.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide; N-ethyl-N,N-diisopropylamine / 20 °C 4.1: ethyl acetate / 12 h / 120 °C 5.1: hydrogenchloride; water / ethyl acetate / 0.5 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: benzotriazol-1-ol / dichloromethane / 0.17 h / -10 °C 1.2: 0.5 h 1.3: 20 °C 2.1: lithium hydroxide monohydrate / methanol; water / 2 h 3.1: benzotriazol-1-ol / dichloromethane / 0.17 h / -10 °C 3.2: 0.5 h 4.1: Dihydroxy-isobutyl-boran; hydrogenchloride / methanol; water; hexane View Scheme
Multi-step reaction with 5 steps 1: acetonitrile / 1 h / 20 °C / Inert atmosphere 2: sodium hydroxide; water / 1 h / 0 - 10 °C 3: acetonitrile / 20 - 30 °C 4: 1 h / 0 - 10 °C 5: hydrogenchloride / di-isopropyl ether / 5 h / 20 °C View Scheme

: (S)-N-(2,5-dichlorobenzoyl)glycine methyl ester

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: lithium hydroxide; water / tetrahydrofuran / 0.5 h / 20 °C 2: benzotriazol-1-ol; dicyclohexyl-carbodiimide; N-ethyl-N,N-diisopropylamine / 20 °C 3: ethyl acetate / 12 h / 120 °C 4: hydrogenchloride; water / ethyl acetate / 0.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / methanol; water / 2 h 2.1: benzotriazol-1-ol / dichloromethane / 0.17 h / -10 °C 2.2: 0.5 h 3.1: Dihydroxy-isobutyl-boran; hydrogenchloride / methanol; water; hexane View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / water; acetone / 2 h / 0 °C 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -10 - -5 °C 3: hydrogenchloride / water; acetone / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / water; acetone / 2 h / 0 °C 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / -10 - -5 °C 3: hydrogenchloride / water; acetone / 40 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: lithium hydroxide monohydrate / methanol; water / 3 h / 20 °C / Cooling with ice 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.67 h / -5 °C 2.2: 6.67 h / 20 °C 3.1: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; hexane / 20 °C View Scheme

: 667403-46-5
2-[(2,5-dichlorobenzoyl)amino]acetic acid

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: benzotriazol-1-ol; dicyclohexyl-carbodiimide; N-ethyl-N,N-diisopropylamine / 20 °C 2: ethyl acetate / 12 h / 120 °C 3: hydrogenchloride; water / ethyl acetate / 0.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol / dichloromethane / 0.17 h / -10 °C 1.2: 0.5 h 2.1: Dihydroxy-isobutyl-boran; hydrogenchloride / methanol; water; hexane View Scheme
Multi-step reaction with 3 steps 1: acetonitrile / 20 - 30 °C 2: 1 h / 0 - 10 °C 3: hydrogenchloride / di-isopropyl ether / 5 h / 20 °C View Scheme

: C12H9Cl2N3O2

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1 h / 0 - 10 °C 2: hydrogenchloride / di-isopropyl ether / 5 h / 20 °C View Scheme

: C10H6Cl2N2O

: 1072833-77-2
Ixazomib

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; water / 1 h / 0 - 10 °C 2: acetonitrile / 20 - 30 °C 3: 1 h / 0 - 10 °C 4: hydrogenchloride / di-isopropyl ether / 5 h / 20 °C View Scheme

: 1072833-77-2
Ixazomib

: 111-42-2
2,2'-iminobis[ethanol]

: 2,5-dichloro-N-[(2-((1R)-3-methyl-1-[1,3,6,2]-dioxaborolan-2-yl)-butylamino)-2-oxyethyl]benzamide

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 2h; Product distribution / selectivity;	100%

: 1072833-77-2
Ixazomib

: 77-92-9
citric acid

: 2,2’-{2-[(1R)-1-({[(2,5-dichlorobenzoyl)amino]acetyl}amino)-3-methylbutyl]-5-oxo-1,3,2-dioxaborolane-4,4-diyl}diacetic acid

Conditions

Conditions	Yield
In acetone at 20℃; for 0.5h;	95%
In ethyl acetate at 60℃; for 0.5h;

: 1072833-77-2
Ixazomib

: 77-92-9
citric acid

: 1201902-80-8
4-(carboxymethyl)-2-((R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutyl)-6-oxo-1,3,2-dioxaborinane-4-carboxylic acid

Conditions

Conditions	Yield
In ethyl acetate at 60 - 74℃; for 3h;	94%

: 1072833-77-2
Ixazomib

: 111-42-2
2,2'-iminobis[ethanol]

: N-(R)-(2-((1-(1,3,6,2-dioxazaborocan-2-yl)-3-methylbutyl)amino)-2-oxoethyl)-2,5-dichlorobenzamide

Conditions

Conditions	Yield
In ethyl acetate at 20 - 74℃; for 3h;	85.4%
In ethyl acetate at 60 - 74℃; for 3h;	557 mg

: 1072833-77-2
Ixazomib

: N-methylimino diacetic acid

: 2,5-dichloro-N-{[(R)-3-methyl-1-(6-methyl-4,8-dioxo-[1,3,6,2]dioxazaborolan-2-yl)-butylcarbamoyl]methyl}-benzamide

Conditions

Conditions	Yield
In dimethyl sulfoxide; toluene for 18h; Reflux;	83.4%

: 1072833-77-2
Ixazomib

: C14H29N3O6

: C28H44BCl2N5O8

Conditions

Conditions	Yield
In chloroform-d1	67%

: 105-59-9
N-Methyldiethanolamine

: 1072833-77-2
Ixazomib

: 2,5-dichloro-N-{[(R)-3-methyl-1-(6-methyl-[1,3,6,2]dioxazaborolan-2-yl)-butylcarbamoyl]methyl}-benzamide

Conditions

Conditions	Yield
In ethyl acetate at 20℃;	66%

: 1072833-77-2
Ixazomib

: 110-97-4
diisopropanolamine

: 2,5-dichloro-N-[(R)-1-(4,8-dimethyl-[1,3,6,2]dioxazaborolan-2-yl)-3-methyl-(butylcarbamoyl)methyl]-benzamide

Conditions

Conditions	Yield
In ethyl acetate at 20℃;	64%

: 1072833-77-2
Ixazomib

: 611-71-2
(R)-Mandelic Acid

: 1201902-85-3
2-chloro-5-chloro-N-[2-({(1R)-3-methyl-1-[(5R)-4-oxo-5-phenyl-1,3,2-dioxaborolan-2-yl]butyl}amino)-2-oxoethyl]benzamide

Conditions

Conditions	Yield
In ethyl acetate for 0.666667h;	57%

: 1072833-77-2
Ixazomib

: (R)-(1-(2-(2,5-dichlorobenzamido)-d2-acetamido)-3-methylbutyl)boronic acid

Conditions

Conditions	Yield
With dimethylsulfoxide-d6; water-d2; potassium carbonate In tetrahydrofuran at 65℃; for 5h;	55.6%
With water-d2; sodium methylate at 0℃; for 72h;	630 mg

: 102-71-6
triethanolamine

: 1072833-77-2
Ixazomib

: N-(R)-(2-((1-(6-(2-hydroxyethyl)-1,3,6,2-dioxazaborocan-2-yl)-3-methylbutyl)amino)-2-oxoethyl)-2,5-dichlorobenzamide

Conditions

Conditions	Yield
In ethyl acetate at 20 - 74℃; for 3h;	53.3%

: 1072833-77-2
Ixazomib

: C20H21(2)H2BCl2N2O9

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water-d2; sodium methylate / 72 h / 0 °C 2: ethyl acetate / 48 h / 40 °C View Scheme

: 78468-60-7
D2-citric acid

: 1072833-77-2
Ixazomib

: C20H21(2)H2BCl2N2O9

Conditions

Conditions	Yield
In acetic acid butyl ester at 90℃; for 14h;	51 mg

: 1072833-77-2
Ixazomib

: D4-citric acid

: C20H19(2)H4BCl2N2O9

Conditions

Conditions	Yield
In acetic acid butyl ester at 90℃; for 14h;	53 mg

: 1072833-77-2
Ixazomib

: C19H19N3O9

: C33H34BCl2N5O11

Conditions

Conditions	Yield
In ethyl acetate at 20℃;

: 1072833-77-2
Ixazomib

Reaxys ID: 36479190: Reaxys ID: 36479190

Reaxys ID: 36479266: Reaxys ID: 36479266

: 1072833-77-2
Ixazomib

Reaxys ID: 36479191: Reaxys ID: 36479191

Reaxys ID: 36479267: Reaxys ID: 36479267

MLN-2238 Specification

The MLN-2238, with the CAS registry number of 1072833-77-2, is also known as (R)-1-(2-(2,5-Dichlorobenzamido)acetamido)-3-methylbutylboronic acid. This chemical's molecular formula is C₁₄H₁₉BCl₂N₂O₄. What's more, its systematic name is [(1R)-1-[[2-[(2,5-Dichlorobenzoyl)amino]acetyl]amino]-3-methyl-butyl]boronic acid.

Physical properties about the MLN-2238 are: (1)ACD/LogP: 2.31; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.31; (4)ACD/LogD (pH 7.4): 2.309; (5)ACD/BCF (pH 5.5): 33.566; (6)ACD/BCF (pH 7.4): 33.457; (7)ACD/KOC (pH 5.5): 430.378; (8)ACD/KOC (pH 7.4): 428.978; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 98.66 Å²; (13)Index of Refraction: 1.546; (14)Molar Refractivity: 87.504 cm³; (15)Molar Volume: 276.372 cm³; (16)Surface Tension: 48.422 dyne/cm; (17)Density: 1.306 g/cm³.

You can still convert the following datas into molecular structure:
(1) SMILES: B([C@H](CC(C)C)NC(=O)CNC(=O)c1cc(ccc1Cl)Cl)(O)O
(2) InChI: InChI=1/C14H19BCl2N2O4/c1-8(2)5-12(15(22)23)19-13(20)7-18-14(21)10-6-9(16)3-4-11(10)17/h3-4,6,8,12,22-23H,5,7H2,1-2H3,(H,18,21)(H,19,20)/t12-/m0/s1
(3) InChIKey: MXAYKZJJDUDWDS-LBPRGKRZBV

Product Name

(R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acid

Synthetic route

MLN-2238 Specification

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