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361442-04-8

Basic Information
CAS No.: 361442-04-8
Name: Saxagliptin
Article Data: 2
Molecular Structure:
Molecular Structure of 361442-04-8 (Saxagliptin)
Formula: C18H25N3O2
Molecular Weight: 315.415
Synonyms: 2-Azabicyclo(3.1.0)hexane-3-carbonitrile, 2-((2S)-amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl) , (1S,3S,5S)-;(1S,3S,5S)-2-[(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile;(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile;2-azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-;
EINECS: 1308068-626-2
Density: 1.35 g/cm3
Boiling Point: 548.7 °C at 760 mmHg
Flash Point: 285.6 °C
Appearance: White powder
Risk Codes: 28-38-41-48
Safety: 24/25-26-28-36/37/39
PSA: 90.35000
LogP: 1.79618
Synthetic route

saxaglipitin

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 20℃; for 1h; pH=9;

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide hydrochloride

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere
1.2: .(R).T3P / 17.5 h / 0 - 25 °C
2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
2.2: 20 - 25 °C / pH > 10
3.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C
3.2: pH > 11
View Scheme

3-(aminocarbonyl)-(3,7]dec-1-yl)-

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
1.2: 20 - 25 °C / pH > 10
2.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C
2.2: pH > 11
View Scheme

(3,7]decane-1-acetic acid

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere
1.2: .(R).T3P / 17.5 h / 0 - 25 °C
2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
2.2: 20 - 25 °C / pH > 10
3.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C
3.2: pH > 11
View Scheme

[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-2-oxoethyl]carbamic acid-1,1-dimethylethyl ester

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Stage #1: [(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-2-oxoethyl]carbamic acid-1,1-dimethylethyl ester With hydrogenchloride; water In methanol; dichloromethane at 0 - 20℃; for 20.6667h;
Stage #2: With sodium hydroxide In water pH=> 11;

(R)-N-boc-3-hydroxyadamant-1-yl glycine

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 4.5 h / 20 - 25 °C
1.2: 38 h / 20 - 25 °C
1.3: 0.67 h
2.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere
2.2: .(R).T3P / 17.5 h / 0 - 25 °C
3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
3.2: 20 - 25 °C / pH > 10
4.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C
4.2: pH > 11
View Scheme

racemic N-boc-3-hydroxyadamant-1-yl glycine

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 3.33 h / 70 °C
2.1: hydrogenchloride; water / ethyl acetate; water / pH 3
3.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere
3.2: .(R).T3P / 17.5 h / 0 - 25 °C
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
4.2: 20 - 25 °C / pH > 10
5.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C
5.2: pH > 11
View Scheme
Multi-step reaction with 6 steps
1.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 3.33 h / 70 °C
2.1: hydrogenchloride; water / ethyl acetate; water / pH 3
3.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 4.5 h / 20 - 25 °C
3.2: 38 h / 20 - 25 °C
3.3: 0.67 h
4.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere
4.2: .(R).T3P / 17.5 h / 0 - 25 °C
5.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
5.2: 20 - 25 °C / pH > 10
6.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C
6.2: pH > 11
View Scheme

(S)-N-boc-3-hydroxyadamant-1-yl glycine amine

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride; water / ethyl acetate; water / pH 3
2.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere
2.2: .(R).T3P / 17.5 h / 0 - 25 °C
3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
3.2: 20 - 25 °C / pH > 10
4.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C
4.2: pH > 11
View Scheme

(R)-N-boc-3-hydroxyadamant-1-yl glycine amine

361442-04-8

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride; water / ethyl acetate; water / pH 3
2.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 4.5 h / 20 - 25 °C
2.2: 38 h / 20 - 25 °C
2.3: 0.67 h
3.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere
3.2: .(R).T3P / 17.5 h / 0 - 25 °C
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C
4.2: 20 - 25 °C / pH > 10
5.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C
5.2: pH > 11
View Scheme
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    Product Name: Saxagliptin Synonyms: Saxagliptin;(1S,3S,5S)-2-[(2S)-2-Amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile;BMS 477118;Onglyza;Saxaglip

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Specification

The CAS registry number of Saxagliptin is 361442-04-8. The IUPAC name is (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile. In addition, the molecula formula is C18H25N3O2 and the molecular weight is 315.41. It is a putative antidiabetic agent for treating type 2 diabetes. And it can inhibit DPP4 protein.

Physical properties about this chemical are: (1)ACD/LogP: -0.14; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.73; (4)ACD/LogD (pH 7.4): -1.04; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 2.51; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 56.57 Å2; (13)Index of Refraction: 1.64; (14)Molar Refractivity: 84.16 cm3; (15)Molar Volume: 233.6 cm3; (16)Polarizability: 33.36 ×10-24cm3; (17)Surface Tension: 68.3 dyne/cm; (18)Density: 1.35 g/cm3; (19)Flash Point: 285.6 °C; (20)Enthalpy of Vaporization: 95.22 kJ/mol; (21)Boiling Point: 548.7 °C at 760 mmHg; (22)Vapour Pressure: 2.51E-14 mmHg at 25°C.

Preparation of Saxagliptin: it can be prepared by N-Boc-3-hydroxyadamantylglycine and methanoprolineamide with EDC. The prolineamide moiety is subsequently dehydrated with trifluoroacetic anhydride to give the cyanide as the trifluoracetate ester, which is hydrolyzed.

Saxagliptin can be prepared by N-Boc-3-hydroxyadamantylglycine and methanoprolineamide with EDC

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N1[C@H](C#N)C[C@@H]2C[C@H]12)[C@@H](N)C35CC4CC(C3)CC(O)(C4)C5
(2)InChI: InChI=1/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10?,11?,12-,13+,14+,15-,17?,18?/m1/s1
(3)InChIKey: QGJUIPDUBHWZPV-SGTAVMJGBR