Structure of (S)-3-N-Cbz-Amino-succinimide
CAS No.: 60846-91-5
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 60846-91-5 |
Formula : | C12H12N2O4 |
M.W : | 248.24 |
SMILES Code : | O=C(N1)C[C@H](NC(OCC2=CC=CC=C2)=O)C1=O |
MDL No. : | MFCD05864630 |
InChI Key : | QRQMHYISDDHZBY-VIFPVBQESA-N |
Pubchem ID : | 10083340 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 64.92 |
TPSA ? Topological Polar Surface Area: Calculated from |
84.5 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.41 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.31 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.55 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.78 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.57 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.49 |
Solubility | 8.01 mg/ml ; 0.0323 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.65 |
Solubility | 5.59 mg/ml ; 0.0225 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.26 |
Solubility | 0.137 mg/ml ; 0.000553 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.59 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.64 |
* 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 hydrogen;5% palladium over charcoal; In methanol; under 1034.32 Torr; for 4h; | Example -1; (3S)-3-(3-Cyclopentyloxy-4-methoxyphenylcarboxamido)-2,5-dioxoazolane. Step 1: (3S)-3-Aminoazolane-2,5-dione was prepared as follows: To a solution of (3S)-3-(N-Cbz-amino)azolane-2,5-dione ( 4.0 g, 16.12 mmol) in methanol (40 ml) was added 5 % palladium on carbon (50 mg) and was stirred under 20 psi 10 hydrogen pressure for 4 h. The mixture was filtered through a celite bed to remove the catalyst. The solvent was evaporated under reduced pressure to give 1.6 g of the product as pale yellow viscous liquid which was used as such for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In DMF (N,N-dimethyl-formamide); at 80℃; for 6h; | Intermediate 6; (3S)-3-(N-Cbz-Amino)azolane-2,5-dione. To a stirred solution of N(alpha)-Cbz-L-asparagine (10 g, 37.5 mmol) dissolved in DMF (50 ml) was added DCC (7.8 g, 37.5 mmol) and N-hydroxysuccinimide (4.4 g, 37.5 mmol) and the mixture was heated at 80 C for 6 h. DMF was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (100 ml) and filtered to remove DCU. The filterate was washed with water (2 x 100 ml), brine (100 ml) and dried (Na2SO4). The product obtained after evaporation of the solvent was purified by silica gel column chromatography using 50 % ethyl acetate in petroleum ether to give 4.2 g of the product as white solid, mp 66-69 C; IR (KBr) 3395, 3177, 2936, 2749, 1723, 1689, 1519, 1260, 1177 cm-1; 1H NMR (300 MHz, CDC13) 5 2.81-2.89 (m, 1 H), 3.04-3.13 (m, 1 H), 4.33-4.40 (m, 1 H), 5.11 (s, 2 H), 4.63 (brs, 1 H), 7.34 (s, 5 H), 8.54 (brs, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 9; (3S)-3-(N-Cbz-Amino)-1 -cyanomethylazolane-2,5-dione. To a stirred solution of the solution (3S)-3-(N-Cbz-amino)-2,5-dioxoazolane (550 mg, 2.215 mmol) in dry DMF (10 ml) was added cesium hydroxide monohydrate (446 mg, 2.658 mmol) and the mixture was stirred at rt for 10 min. Chloroacetonitrile (230 mg, 3.046 mmol) was added and further stirred at rt for 1.5 h. The reaction mixture was quenched with ice cold water and acidified with IN HC1. The mixture was extracted with ethyl acetate (2 x 20 ml). The organic layer was washed with water (20 ml) and brine (20 ml) and dried (Na2SO4). The crude product obtained after evaporation of the solvent was purified by silica gel column chromatography using 25 % EtOAc in petroleum ether as eluent to give 452 mg of the product as white solid; IR (KBr) 3370, 2949, 2242, 1721, 1523, 1261, 1171 cm-1; 1HNMR (300 MHz, CDC13) delta 2.91 (dd,7= 18.3, 5.7 Hz, 1 H), 3.15 (dd, J= 18.3, 9.2 Hz, 1 H), 4.30-4.37 (m, 1 H), 4.42 (s, 2 H), 5.05 (dd, J = 14.7,12.0, 2 H), 5.58 (brs, 1 H), 7.32-7.39 (m, 5 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35%; 11% | General procedure: To a solution of 1a (113 mg, 1 mmol), 2a (384 mg, 2 mmol), and zinc powder (0.26 g, 4 mmol) in THF (10 mL) was added TiCl4 (0.22 mL, 2 mmol) dropwise at 0 C and then the dark blue suspension was stirred for 12 h at this temperature. To the mixture was added 1M HCl (20 mL) and the mixture was stirred for 15 min at 25 C. The clear solution was extracted with ethyl acetate three times. The organic layer was washed with aqueous NaCl and dried over MgSO4. After the solvent was removed in vacuo, the residuewas dissolved in benzene (10 mL). The solution was refluxed in the presence of cat. p-TsOH for 30 min using Dean-Stark apparatus.After the solvent was removed in vacuo, the residue was purified by column chromatography on silica gel to give 3a. |
A141655 [223407-18-9]
(R)-Benzyl (2-oxopyrrolidin-3-yl)carbamate
Similarity: 0.97
A446509 [1219424-59-5]
Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate
Similarity: 0.92
A141655 [223407-18-9]
(R)-Benzyl (2-oxopyrrolidin-3-yl)carbamate
Similarity: 0.97
A446509 [1219424-59-5]
Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate
Similarity: 0.92
A141655 [223407-18-9]
(R)-Benzyl (2-oxopyrrolidin-3-yl)carbamate
Similarity: 0.97
A446509 [1219424-59-5]
Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate
Similarity: 0.92
A105115 [1217631-74-7]
(S)-Benzyl pyrrolidin-3-ylcarbamate hydrochloride
Similarity: 0.82
A141655 [223407-18-9]
(R)-Benzyl (2-oxopyrrolidin-3-yl)carbamate
Similarity: 0.97
A446509 [1219424-59-5]
Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate
Similarity: 0.92
A105115 [1217631-74-7]
(S)-Benzyl pyrrolidin-3-ylcarbamate hydrochloride
Similarity: 0.82
A216700 [1217652-74-8]
(R)-Benzyl (pyrrolidin-2-ylmethyl)carbamate hydrochloride
Similarity: 0.80