N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester
nateglinide
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; |
trans-4-isopropylcyclohexane-1-carboxylic acid
D-(R)-phenylalanine
chloroformic acid ethyl ester
A
N-(ethoxycarbonyl)-(D)-phenylalanine
B
nateglinide
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 |
Conditions | Yield |
---|---|
In dichloromethane at 25 - 30℃; for 18.5h; | 75% |
D-(R)-phenylalanine
4-iso-propylcyclohexanecarbonyl chloride
nateglinide
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 |
trans-4-iso-propylcyclohexylcarbonyl chloride
nateglinide
Conditions | Yield |
---|---|
In acetonitrile at -5 - 0℃; for 3.58333 - 3.66667h; Heating / reflux; |
trans-4-isopropylcyclohexane-1-carboxylic acid
nateglinide
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 |
D-phenylalanine methyl ester
nateglinide
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 |
p-menthan-7-oic acid methyl ester
nateglinide
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 |
C19H26NO3(1-)*K(1+)
nateglinide
Conditions | Yield |
---|---|
With hydrogenchloride In water at 15 - 20℃; pH=2.0 - 3.0; Product distribution / selectivity; |
C19H26NO3(1-)*Na(1+)
nateglinide
Conditions | Yield |
---|---|
With hydrogenchloride; water at 25℃; for 0.5h; pH=2 - 3; Product distribution / selectivity; |
D-(R)-phenylalanine
4-iso-propylcyclohexanecarbonyl chloride
nateglinide
Conditions | Yield |
---|---|
With sodium hydroxide; sulfuric acid In n-heptane |
trans-4-isopropylcyclohexane-1-carboxylic acid
D-(R)-phenylalanine
nateglinide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: thionyl chloride / 12.5 h / 5 - 25 °C / Inert atmosphere 1.2: 0.25 h / 25 °C / Inert atmosphere 1.3: 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 |
D-(R)-phenylalanine
nateglinide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: thionyl chloride / 12.5 h / 5 - 25 °C / Inert atmosphere 2.1: ammonia / dichloromethane; water / 0.5 h / 10 °C 3.1: benzotriazol-1-ol / dichloromethane / 0.25 h / 25 °C / Inert atmosphere 3.2: 3.25 h / 0 - 15 °C 4.1: sodium hydroxide / acetone / 2 h / 20 - 25 °C 4.2: 1 h / 10 °C / pH 2 - 3 View Scheme | |
Multi-step reaction with 3 steps 1.1: thionyl chloride / 12.5 h / 5 - 25 °C / Inert atmosphere 2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 25 °C / Inert atmosphere 2.2: 3 h / 0 - 15 °C 3.1: sodium hydroxide / acetone / 2 h / 20 - 25 °C 3.2: 1 h / 10 °C / pH 2 - 3 View Scheme |
D-phenylalanine methyl ester hydrochloride
nateglinide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ammonia / dichloromethane; water / 0.5 h / 10 °C 2.1: benzotriazol-1-ol / dichloromethane / 0.25 h / 25 °C / Inert atmosphere 2.2: 3.25 h / 0 - 15 °C 3.1: sodium hydroxide / acetone / 2 h / 20 - 25 °C 3.2: 1 h / 10 °C / pH 2 - 3 View Scheme |
trans-4-iso-propylcyclohexylcarbonyl chloride
D-(R)-phenylalanine
nateglinide
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 20℃; for 20h; Temperature; | 70 g |
4-(1-hydroxyethyl)benzyl alcohol
nateglinide
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 97% |
methanol
nateglinide
N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester
Conditions | Yield |
---|---|
With sulfuric acid Reflux; | 97% |
nateglinide
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In dimethyl sulfoxide Irradiation; Inert atmosphere; Sealed tube; | 53% |
nateglinide
ethyl acrylate
Conditions | Yield |
---|---|
With Ir(dF(CF3)ppy)2(bpy)PF6; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Sealed tube; Inert atmosphere; Irradiation; | 44% |
3-(nitrooxymethyl)benzyl alcohol
nateglinide
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h; | 32% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h; | 23% |
diisopropylamine
nateglinide
Conditions | Yield |
---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide 1) CHCl3, 1 d, 2) CHCl3, 25 deg C, 1 d; Yield given. Multistep reaction; |
nateglinide
Conditions | Yield |
---|---|
With ammonium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide 1) CHCl3, 1 d, 2) CHCl3, 25 deg C, 1 d; Yield given. Multistep reaction; |
nateglinide
Conditions | Yield |
---|---|
Stage #1: nateglinide In methanol; water at 39℃; for 0.5h; pH=4; Stage #2: With ammonia In methanol; water at 0℃; for 1h; pH=5; | |
Stage #1: nateglinide In water; acetone at 35℃; Stage #2: In water; acetone at -10℃; for 3h; |
ethanol
nateglinide
ethyl (trans-4-isopropylcyclohexane-1-carbonyl)-D-phenylalaninate
Conditions | Yield |
---|---|
With thionyl chloride |
Conditions | Yield |
---|---|
at 25℃; |
Conditions | Yield |
---|---|
at 25℃; |
Conditions | Yield |
---|---|
at 25℃; |
Conditions | Yield |
---|---|
at 25℃; |
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, |
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