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Basic Information

Molecular Structure:
CAS No.:	105816-04-4
Name:	Nateglinide
Article Data:	14

Formula:	C₁₉H₂₇NO₃
Molecular Weight:	317.428
Synonyms:	Nateglinide [INN];Fastic;trans-N-((4-(1-Methylethyl)cyclohexyl)carbonyl)-D-phenylalanine;A 4166;Starlix;Nateglinide(105816-04-4 );Nateglinide,105816-04-4;Starsis (TN);(2R)-3-phenyl-2-[[(1S,3S)-3-propan-2-ylcyclohexanecarbonyl]amino]propanoic acid;D-Phenylalanine,N-[[trans-4-(1-methylethyl)- cyclohexyl]carbonyl]-;Starsis;(-)-N-(trans-4-Isopropylcyclohexanecarbonyl)-D-phenylalanine;Nateglynide;Nateglinide intermediate;Nateglinide-H;AY 4166;D-Phenylalanine, N-((4-(1-methylethyl)cyclohexyl)carbonyl)-, trans-;
Density:	1.104 g/cm³
Melting Point:	137-141 °C
Boiling Point:	527.6 °C at 760 mmHg
Flash Point:	272.9 °C
Appearance:	white crystalline powder
Hazard Symbols:	Xn
Risk Codes:	22
Safety:	24/25-36
PSA:	66.40000
LogP:	3.65180

Synthetic route

: 105746-47-2
N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
Stage #1: N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester With water; sodium hydroxide In methanol at 25 - 30℃; for 5h; Stage #2: With hydrogenchloride In water pH=2.0 - 2.5;	80.8%
With sodium hydroxide In methanol Yield given;
Stage #1: N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester With sodium hydroxide In acetone at 20 - 25℃; for 2h; Stage #2: With hydrogenchloride In water at 10℃; for 1h; pH=2 - 3; Product distribution / selectivity;

: 7077-05-6
trans-4-isopropylcyclohexane-1-carboxylic acid

: 673-06-3
D-(R)-phenylalanine

: 541-41-3
chloroformic acid ethyl ester

A: 21488-23-3
N-(ethoxycarbonyl)-(D)-phenylalanine

B: 105816-04-4
nateglinide

C: 2-[2-[(trans-4-isopropylcyclohexanecarbonyl)amino]-3-phenylpropionylamino]-3-phenylpropionic acid

Conditions

Conditions	Yield
Stage #1: trans-4-isopropylcyclohexane-1-carboxylic acid; chloroformic acid ethyl ester With triethylamine In acetone at -10 - -5℃; for 1.25h; Stage #2: D-(R)-phenylalanine With 4-methyl-morpholine; triethylamine In water; acetone at -10 - -5℃;	A n/a B 80% C n/a

...Expand

: 1245809-48-6
C17H24O4S

: 673-06-3
D-(R)-phenylalanine

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
In dichloromethane at 25 - 30℃; for 18.5h;	75%

: 673-06-3
D-(R)-phenylalanine

: 100597-38-4
4-iso-propylcyclohexanecarbonyl chloride

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
With sodium hydroxide; sulfuric acid	65%
With sodium hydroxide; sulfuric acid In n-heptane; ethyl acetate	65%
With potassium hydroxide In water; acetone

: 84855-54-9
trans-4-iso-propylcyclohexylcarbonyl chloride

: N,O-bis trimethylsilyl D-phenylalanine

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
In acetonitrile at -5 - 0℃; for 3.58333 - 3.66667h; Heating / reflux;

: 7077-05-6
trans-4-isopropylcyclohexane-1-carboxylic acid

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) CHCl3, 3 h, 2) CHCl3, 25 deg C, 1 d 2: 2N NaOH / methanol View Scheme

: 21685-51-8
D-phenylalanine methyl ester

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) CHCl3, 3 h, 2) CHCl3, 25 deg C, 1 d 2: 2N NaOH / methanol View Scheme
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol / dichloromethane / 0.25 h / 25 °C / Inert atmosphere 1.2: 3.25 h / 0 - 15 °C 2.1: sodium hydroxide / acetone / 2 h / 20 - 25 °C 2.2: 1 h / 10 °C / pH 2 - 3 View Scheme

: 175284-00-1
p-menthan-7-oic acid methyl ester

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) NaH, 2) 2N aq. NaOH / 1) 150 deg C, 2 h, 2) MeOH, 20 deg C, 10 min 2: 1) N-hydroxysuccinimide, dicyclohexylcarbodiimide / 1) CHCl3, 3 h, 2) CHCl3, 25 deg C, 1 d 3: 2N NaOH / methanol View Scheme

: 594837-86-2
C19H26NO3(1-)*K(1+)

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
With hydrogenchloride In water at 15 - 20℃; pH=2.0 - 3.0; Product distribution / selectivity;

: 594837-85-1
C19H26NO3(1-)*Na(1+)

: 105816-04-4
nateglinide

Conditions

Conditions	Yield
With hydrogenchloride; water at 25℃; for 0.5h; pH=2 - 3; Product distribution / selectivity;

Raw Materials

673-06-3

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Specification

The CAS registry number of Nateglinide is 105816-04-4. The systematic name is N-{[trans-4-(propan-2-yl)cyclohexyl]carbonyl}-D-phenylalanine. In addition, the molecular formula is C₁₉H₂₇NO₃ and the molecular weight is 317.42. What's more, it belongs to the meglitinide class of blood glucose-lowering drugs. It is a drug for the treatment of type 2 diabetes. And it can be used as an amino-acid derivative that stimulates insulin secretion. Besides, it also can be used as an antidiabetic.

Physical properties about this chemical are: (1)ACD/LogP: 2.35; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 5; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 27; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 66.4 Å²; (12)Index of Refraction: 1.536; (13)Molar Refractivity: 89.612 cm³; (14)Molar Volume: 287.347 cm³; (15)Polarizability: 35.525 ×10^-24cm³; (16)Surface Tension: 44.58 dyne/cm; (17)Density: 1.105 g/cm³; (18)Flash Point: 272.869 °C; (19)Enthalpy of Vaporization: 84.443 kJ/mol; (20)Boiling Point: 527.578 °C at 760 mmHg.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. During using it, wear suitable protective clothing and you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N[C@H](Cc1ccccc1)C(O)=O)[C@H]2CC[C@@H](CC2)C(C)C
(2)InChI: InChI=1/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1
(3)InChIKey: OELFLUMRDSZNSF-BRWVUGGUBB

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD	oral	> 2gm/kg (2000mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25(Suppl,
rat	LD	oral	> 2gm/kg (2000mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 25(Suppl,