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CAS No. : | 60421-23-0 | MDL No. : | MFCD03840364 |
Formula : | C7H14ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OPUJUITUYWGUEP-UHFFFAOYSA-N |
M.W : | 179.64 | Pubchem ID : | 11513856 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 44.64 |
TPSA : | 52.32 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.64 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.07 |
Log Po/w (WLOGP) : | 1.23 |
Log Po/w (MLOGP) : | 0.69 |
Log Po/w (SILICOS-IT) : | 0.77 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.5 |
Solubility : | 5.73 mg/ml ; 0.0319 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.76 |
Solubility : | 3.12 mg/ml ; 0.0174 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.95 |
Solubility : | 20.2 mg/ml ; 0.112 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.51 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride In methanol at -15 - 20℃; | To a suspension of 1-aminocyclopentanecarboxylic acid, (675 g, 5.23 mol, 1.0 equiv.) in MeOH (6.5 L) held at -15° C. with an ice/MeOH bath was added SOCl2 (687 mL, 9.4 mol, 1.8 equiv.), dropwise at such a rate that the reaction temp. did not exceed 7° C. After the addition was complete, cooling was removed, the reaction was allowed to stir at room temp. overnight, then was concentrated under reduced pressure. The residue was treated with CH2Cl2 (1 L) and concentrated under reduced pressure to afford methyl 1-aminocyclopentanecarboxylate HCl salt as a white solid (938 g, 100percent): 1H NMR (CD3OD) d 1.87-1.94 (m, 8H), 3.83 (s, 3H); NMR (DMSO-d6) δ1.67-1.71 (m, 2H), 1.83-1.98 (m, 4H), 2.06-2.14 (m, 2H), 3.73 (s, 3H), 8.81 (br s 3). This material was used in the next step without further purification |
98% | at 20℃; for 3 h; Cooling with ice | 1-aminocyclopentanecarboxylic acid (3.5 g, 26.9 mmol) and methanol (100 ml) were charged. An ice bath was set and thionyl chloride (3.9 ml, 53.9 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60 oven so as to obtain methyl-1-aminocyclopentanecarboxylate hydrochloride (4.74 g, 26.4 mmol, 98 percent).[823] 1H NMR (400 MHz, DMSO-d6) δ 8.76 (br, 3H), 3.75 (s, 3H), 2.12 (m, 2H), 1.88 (m, 4H), 1.72 (m, 2H). |
98% | at 20℃; for 3 h; Inert atmosphere | Preparation Example 1 Synthesis of N-4-(1-(3-chloro-2-methylphenylsulfonamido)cyclopentanecarboxyamido)adamantane-1-carboxyamide (compound 167) 1-aminocyclopentanecarboxylic acid (3.5 g, 26.9 mmol) and methanol (100 ml) were charged. An ice bath was set and thionyl chloride (3.9 ml, 53.9 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60° C. oven so as to obtain methyl-1-aminocyclopentanecarboxylate hydrochloride (4.74 g, 26.4 mmol, 98percent). 1H NMR (400 MHz, DMSO-d6) δ 8.76 (br, 3H), 3.75 (s, 3H), 2.12 (m, 2H), 1.88 (m, 4H), 1.72 (m, 2H). |
97% | at 20℃; | 1-Amino-l-cyclopentanecarboxylic acid (5.00 g, 38.8 mmol) was dissolved in methanol (100 mL) and then thionyl chloride (9.25 g, 77.7 mmol) was added dropwise with stirring. The resulting mixture was stirred overnight at room temperature and then concentrated in vacuo which left a white solid. The solid was tritruated in ethyl ether, filtered, and dried to give 6.78 g (97 percent) of methyl 1-amino- 1-cyclopentanecarboxylate hydrochloride as a white solid. 1H NMR was consistent with product. ESMS (M+1) 144.2 |
97% | for 18 h; | 1-Aminocyclopentanecarboxylic acid (1.00 g, 7.74 mmol) was added to a solution of acetyl chloride (0.60 mL, 8.44 mmol) in methanol (10 mL). The reaction mixture was allowed to stir for EPO <DP n="37"/>18 h and then concentrated under reduced pressure. This yielded 1.35 g (97percent) of the title compound. 1H NMR (400 MHz, CD3OD) δ 1.80-2.00 (m, 6H), 2.34-2.39 (m, 2H), 3.82 (s, 3H). |
91% | Reflux | Example 2.1 1-aminocyclopentanecarboxylic acid methyl ester hydrochloride Prepared as a white powder following the general procedure previously described using cycloleucine and methanol. Yield: 91percent Rf (dichloromethane/methanol 9/1): 0.5 MP: 157-159° C. IR: νCO: 1742 cm-1 NMR 1H (DMSO-d6): 1.68-1.84 (m, 6H); 2.04 (m, 2H); 3.71 (s, 3H). Example 2General Procedure for the Preparation of Amino Acid EstersAminocarboxylic acid (1eq) was added at 0° C. to the appropriate alcohol (methanol or ethanol) and the mixture was saturated with anhydrous hydrochloric acid. Thionyl chloride was then added drop by drop. The reaction mixture was stirred at reflux for 12 hours. The reaction mixture was concentrated under reduced pressure and diethyl ether was added to the crude residue. The resulting powder was filtered and washed with diethyl ether. |
89% | Stage #1: at 0℃; for 1 h; Stage #2: for 6 - 16 h; Heating / reflux |
To a stirring solution of anhydrous alcohol (10 mol eq. ) was added thionyl chloride (2 mol eq. ) at 0° C, and the resulting solution stirred for 1 hr. After warming to room temperature, the appropriate amino acid (1 mol eq) was added and the reaction heated at reflux for 6-16 hrs. Removal of solvent and recrystallisation from methanol/ether gave the amino ester hydrochloride salts.; This was synthesised according to Standard Procedure 1, using 1-AMINO-1- cyclopentanecarboxylic acid (3.876 g, 30 mmol) with thionyl chloride (4.44 mL, 45 mmol, ) and anhydrous methanol (15.5 mL). The product was isolated as a white solid (4.81 g, yield 89percent). 'H-NMR (CDC13 ; 300 MHz): 8 9.1 (3H, bs, NH3+Cl), 3.85 (3H, s, OCH3), 2.3-2. 2 (4H, m, 4H cyclopentane), 2. 15 (2H, 2H cyclopentane), 1.95 (2H, m, 2H cyclopentane). 13C-NMR (CDCl3 ; 75 MHz): 8 26.6 (2CH2 cyclopent), 38.1 (2CH2 cyclopent), 54.8 (CH30), 66.6 (cyclopentane), 174.1 (COOMe). |
87% | at 0℃; | General procedure: Thionyl chloride (10 mL) was slowly added to a cold suspension solution of the appropriate aminoacid (50 mmol) in methanol (50 mL) at 0 °C. The reaction mixture was stirred for 8–10 h and thenconcentrated on a rotary evaporator. The white precipitate formed was washed with anhydrous etherand then dried under vacuum. All data agreed with the reported data [43,44]. |
77% | for 1 h; Heating / reflux | Example 10; Methyl 1-[(1-(2,4-dichlorophenyl)-4-methyl-5-{4[(propylsulfonyl)oxy]phenyl}-1H- pyrazol-3-yl) carbonvl1ammo} cvclopentanecarboxylate; Step A Methyl 1-aminocyclopentanecarboxylate hydrochloride; Thionyl chloride (1.5 ml) was dissolved in methanol (15 ml) and poured over 1- aminocyclopentanecarboxylic acid (100 mg, 0.774 mmol). The mixture was refluxed 1 hour. The solvent was evaporated to give the product (107 mg, 77percent). 'H NMR (399.964 MHz) 8 9.00-8. 60 (br, 3H), 3.79 (s, 3H), 2.23 (s, 4H), 2.14-2. 00 (m, 2H), 1.90-1. 76 (m, 2H). |
77% | for 1 h; Heating / reflux | Thionyl chloride (1.5 ml) was dissolved in methanol (15 ml) and poured over 1- Q aminocyclopentanecarboxylic acid (100 mg, 0.774 mmol). The mixture was refluxed 1 hour. The solvent was evaporated to give the product (107 mg, 77percent).1H NMR (399.964 MHz) δ 9.00-8.60 (br, 3H), 3.79 (s, 3H), 2.23 (s, 4H), 2.14-2.00 (m,2H), 1.90-1.76 (m, 2H). |
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