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CAS No. : | 13288-57-8 | MDL No. : | MFCD00038899 |
Formula : | C15H31ClN2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TZBPQINFXPIRBX-MERQFXBCSA-N |
M.W : | 338.87 | Pubchem ID : | 13819885 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.87 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 89.73 |
TPSA : | 90.65 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.8 |
Log Po/w (WLOGP) : | 3.15 |
Log Po/w (MLOGP) : | 1.93 |
Log Po/w (SILICOS-IT) : | 1.81 |
Consensus Log Po/w : | 1.94 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.98 |
Solubility : | 0.356 mg/ml ; 0.00105 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.36 |
Solubility : | 0.0148 mg/ml ; 0.0000436 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.03 |
Solubility : | 0.318 mg/ml ; 0.000938 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.39 |
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 |
---|---|---|
With triethylamine; at 80℃; for 16.1667h;Heating / reflux; | A bioactive group, lysine, was added to the polymeric backbone containing photoreactive group as follows. Mesylate (5.1 g, 10.9 mmol) and TEA (7.6 ml, 5 eq.) were added to a 50 ml round bottom flask fitted with a condenser with stirring under an inert atmosphere. The heterogeneous mixture was heated to 80 C. using an oil bath. Next, bioactive group containing a protecting group, H-Lys(Boc)-OtBu.HCl (BACHEM, 4.0 g, 1.1 eq.), was added in two aliquots over 10 minutes to the stirred reaction. As the reaction mixture approached reflux the reaction solution became more homogeneous and was allowed to stir at the elevated temperature for sixteen hours. After this time, the reaction mixture was filtered, washed with cold methylene chloride twice and the solvent was removed in vacuo. The resulting oil was collected and chromatographed using a gradient of 0?5% methanol/chloroform. Appropriate fractions were collected and re-run on similar column using 0?2% methanol/chloroform. Pooling of the desired fractions gave 830 mg of product. Analysis on an NMR spectrometer was consistent with the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | Preparation 82 Nalpha-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]-Nepsilon-tert-butyloxycarbonyl-L-lysine tert-butyl ester STR190 A solution of 1,4-dichloro-7-isoquinolinylsulphonyl chloride (250 mg, 0.84 mmol), Ne-tert-butyloxycarbonyl-L-lysine tert-butyl ester hydrochloride (286 mg, 0.84 mmol) and triethylamine (235 mul, 1.69 mmol) in CH2 Cl2 (25 ml) was stirred at 23 C. for 3h. The reaction mixture was washed with water (2*20 ml), dried (MgSO4) and concentrated in vacuo to a residue which upon trituration with hexane and then i-Pr2 O gave Nalpha-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-Nepsilon-tert-butyloxycarbonyl-L-lysine tert-butyl ester as a white powder (270 mg, 0.48 mmol). 1 H (CDCl3, 300 MHz) delta 1.1 (9H, s), 1.35-1.5 (13H, m), 1.6-1.85 (2H, m), 3.0-3.2 (2H, m), 3.8-3.95 (1H, m), 4.45-4.6 (1H, br m), 5.35 (1H, d), 8.2 (1H, dd), 8.35 (1H, d), 8.45 (1H, s), 8.8 (1H, d) ppm. LRMS 562 (MH+), 584 (MNa+). Anal. Found: C, 51.04; H, 5.96; N, 7.42. Calc for C24 H33 Cl2 N3 O6 S: C, 51.24; H, 5.91; N, 7.47. | |
With triethylamine; In dichloromethane; | Preparation 82 Nalpha-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]-Nepsilon-tert-butyloxycarbonyl-L-lysine tert-butyl ester A solution of 1,4-dichloro-7-isoquinolinylsulphonyl chloride (250 mg, 0.84 mmol), Nepsilon-tert-butyloxycarbonyl-L-lysine tert-butyl ester hydrochloride (286 mg, 0.84 mmol) and triethylamine (235 mul, 1.69 mmol) in CH2Cl2 (25 ml) was stirred at 23 C. for 3h. The reaction mixture was washed with water (2*20 ml), dried (MgSO4) and concentrated in vacuo to a residue which upon trituration with hexane and then i-Pr2O gave Nalpha-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-Nepsilon-tert-butyloxycarbonyl-L-lysine tert-butyl ester as a white powder (270 mg, 0.48 mmol). 1H (CDCl3, 300 MHz) delta1.1 (9H, s), 1.35-1.5 (13H, m), 1.6-1.85 (2H, m), 3.0-3.2 (2H, m), 3.8-3.95 (1H, m), 4.45-4.6 (1H, br m), 5.35 (1H, d), 8.2 (1H, dd), 8.35 (1H, d), 8.45 (1H, s), 8.8 (1H, d) ppm. LRMS 562 (MH+), 584 (MNa+). Anal. Found: C, 51.04; H, 5.96; N, 7.42. Calc for C24H33Cl2N3O6S:C, 51.24; H, 5.91; N, 7.47. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Cyclohexanecarboxaldehyde (145mul, 1.2mmol) and H-LyS-(BoC)-O1Bu. HCI (302mg, 1 mmol) were stirred in DCM (10ml) at room temperature for 3hr before the addition of NaBH4 (76mg, 2mmol). The reaction was stirred at room temperature for 24hr before being quenched with NaHCO3 (saturated, 20ml) and extracted with DCM (3 x 10ml), The combined organics were dried over Na2SO4, and concentrated in vacuo to yield a brown oil which was dissolved in DCM (10ml) before the addition of triethylamine (560mul, 2mmol) and indole-3-glyoxylyl chloride (415mg, 2mmol). The reaction was stirred at room temperature for 24hr. The solvent was removed in vacuo and the reaction quenched with water (20ml) and extracted with EtOAc (3 x 20ml). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to yield a brown oil. TFA (1 ml) was added to the brown oil in DCM (5ml) and the reaction was stirred at room temperature for 16hr. The solvent was removed in vacuo and purification by preparative HPLC yielded the product, (S)-6-amino-2-{cyclohexylmethyl-[2-(1 H- indol-3-yl)-2-oxo-acetyl]-amino}-hexanoic acid 95, as an off-white solid (72.5mg, 18% yield over 3 steps). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The crude product from Example 1b) (1.380 g, 5.889 mmol) was added to a solution of 1,1'-carbonyldiimidazole (0.955 g, 5.889 mmol) in dimethylformamide (DMF) (21 ml) and stirred at RT for 1 h. Then triethylamine (1.633 ml, 11.780 mmol) and tert-butyl (S)-2-amino-6-tert-butoxycarbonylaminohexanoate hydrochloride (1.996 g, 5.889 mmol) were added, and the mixture was left to stand at RT overnight. The solution was concentrated and partitioned between water and ethyl acetate, and the organic phase was dried over MgSO4, filtered and concentrated. The resulting crude product was purified by preparative HPLC.LC/MS data: Rt(min) 1.757; calc.: [M+H]+=563.76 found: 563.35 (method A) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Commercial tert-butyl(S)-2-amino-6-tert-butoxycarbonylaminohexanoate hydrochloride (1.95 g, 5.75 mmol) was mixed in 30 ml of DMF with NEt3 (0.8 ml, 5.754 mmol) and 1,1'-carbonyldiimidazole (0.933 g, 5.754 mmol) and stirred at RT for 30 min. Then (R)-2-amino-3-cyclohexylpropanoic acid trifluoroacetate (1.64 g, 5.754 mmol) and NEt3 (1.6 ml, 11.5 mmol) were added, and the mixture was heated at 80 C. until the imidazolide formed as intermediate was completely converted. The product was purified by flash chromatography on silica gel (CH2Cl2/MeOH gradient). Yield: 2.1 g (73%) of tert-butyl(S)-6-tert-butoxycarbonylamino-2-[3-((R)-1-carboxy-2-cyclohexylethyl)-ureido]-hexanoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Commercially available tert-butyl(S)-2-amino-6-tert-butoxycarbonylaminohexanoate hydrochloride (89 mg, 0.26 mmol) was mixed in 4 ml of DMF with NEt3 (0.12 ml, 0.53 mmol) and 1,1'-carbonyldiimidazole (43 mg, 0.26 mmol) and stirred at RT for 1 h. Then benzyl[(R)-5-amino-5-((S)-1-carbamoyl-2-methylpropylcarbamoyl)-pentyl]-carbamate hydrochloride (100 mg, 0.24 mmol) was added and the mixture was heated at 80 C. until the imidazolide formed as intermediate was completely converted. Preparative HPLC afforded 76 mg (39%) of tert-butyl(S)-2-{3-[(R)-5-benzyloxycarbonylamino-1-((S)-1-carbamoyl-2-methylpropylcarbamoyl)-pentyl]-ureido}-6-tert-butoxycarbonylaminohexanoate trifluoroacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 10 - 20℃; | A suspension of 5.39 g of H-Lys(Boc)-OtBu hydrochloride (15.9 mmol, 1.0 eq) and 7.1 ml of triethylamine (50.9 mmol, 3.2 eq) in dichloromethane (70 ml) was added to the solution obtained in Example 143d), in such a way that the temperatures did not exceed 10 C. After the addition was complete, the mixture was allowed to reach RT and was stirred for a further 2 h. The reaction mixture was then mixed with 200 ml of 0.2 M hydrochloride acid, and the organic phase was separated off and washed with 100 ml of 0.2 M hydrochloric acid and concentrated. 5.5 g of the desired material were obtained as a colorless oil, which crystallized on standing.LC/MS: Rt(min) 1.76; calc.: [M+H]+ 452.14 found 452.18 (method B). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Cyclohexanecarboxaldehyde (145mui, 1.2mmol) and H-Lys-(Boc)-O'Bu.HCI (302mg, 1 mmol) were stirred in DCM (10ml) at room temperature for 3hr before the addition of NaBH4 (76mg, 2mmol). The reaction was stirred at room temperature for 24hr before being quenched with NaHCO3 (saturated, 20ml) and extracted with DCM (3 x 10ml). The combined organics were dried over Na2SO4, and concentrated in vacuo to yield a brown oil which was dissolved in DCM (10ml) before the addition of triethylamine (560mul, 2mmol) and indole-3-glyoxylyl chloride (415mg, 2mmol). The reaction was stirred at room temperature for 24hr. The solvent was removed in vacuo and the reaction quenched with water (20ml) and extracted with EtOAc (3 x 20ml). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to yield a brown oil. TFA (1ml) was added to the brown oil in DCM (5ml) and the reaction was stirred at room temperature for 16hr. The solvent was removed in vacuo and purification by preparative HPLC yielded the product, (S)-6-amino-2-{cyclohexylmethyl-[2-(1 H- indol-3-yl)~2-oxo-acetyl]-amino}-hexanoic acid 95, as an off-white solid (72.5mg, 18% yield over 3 steps). |
[ 7750-45-0 ]
(S)-tert-Butyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoate hydrochloride
Similarity: 0.95
[ 3350-15-0 ]
(S)-Methyl 2-amino-4-((tert-butoxycarbonyl)amino)butanoate hydrochloride
Similarity: 0.95
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P378 | |
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P391 | Collect spillage. Hazardous to the aquatic environment |
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P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
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Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
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H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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