Home Cart Sign in  
Chemical Structure| 60846-91-5 Chemical Structure| 60846-91-5

Structure of (S)-3-N-Cbz-Amino-succinimide
CAS No.: 60846-91-5

Chemical Structure| 60846-91-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 60846-91-5 ]

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

Safety of [ 60846-91-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 60846-91-5 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

84.5 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.41
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.31
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.2
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.55
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.78
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.57

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.49
Solubility 8.01 mg/ml ; 0.0323 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.65
Solubility 5.59 mg/ml ; 0.0225 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.26
Solubility 0.137 mg/ml ; 0.000553 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.59 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.64

Application In Synthesis of [ 60846-91-5 ]

* 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.

  • Downstream synthetic route of [ 60846-91-5 ]

[ 60846-91-5 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 60846-91-5 ]
  • [ 93185-73-0 ]
  • 3
  • [ 60846-91-5 ]
  • [ 100-39-0 ]
  • [ 124166-11-6 ]
  • 4
  • [ 60846-91-5 ]
  • [ 73537-92-5 ]
YieldReaction ConditionsOperation 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.
  • 5
  • [ 60846-91-5 ]
  • (S)-2-aminosuccinimide hydrobromide [ No CAS ]
  • 6
  • [ 2304-96-3 ]
  • [ 60846-91-5 ]
YieldReaction ConditionsOperation 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).
  • 7
  • [ 64-17-5 ]
  • [ 60846-91-5 ]
  • 3-(N-benzyloxycarbonyl)amino-5-ethoxypyrrolidin-2-one [ No CAS ]
  • 9
  • <i>N</i>-benzyloxycarbonyl-L-asparagine methyl ester [ No CAS ]
  • [ 60846-91-5 ]
  • 10
  • [ 501-53-1 ]
  • (<i>S</i>)-3-amino-pyrrolidine-2,5-dione hydrochloride [ No CAS ]
  • [ 60846-91-5 ]
  • 11
  • [ 501-53-1 ]
  • PhMgX [ No CAS ]
  • [ 60846-91-5 ]
  • 12
  • [ 501-53-1 ]
  • (+-)-2.3-diamino-propionic acid [ No CAS ]
  • [ 60846-91-5 ]
  • 13
  • [ 60846-91-5 ]
  • [ 107-14-2 ]
  • (3S)-3-(N-Cbz-amino)-1-cyanomethylazolane-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 14
  • [ 4668-37-5 ]
  • [ 71-36-3 ]
  • [ 60846-91-5 ]
  • (S)-butyl 4-amino-2-(benzyloxycarbonylamino)-4-oxobutanoate [ No CAS ]
  • 15
  • [ 119-61-9 ]
  • [ 60846-91-5 ]
  • benzyl (5-(diphenylmethylene)-2-oxo-2,5-dihydro-1Hpyrrol-3-yl)carbamate [ No CAS ]
  • benzyl (2-(diphenylmethylene)-5-oxo-2,5-dihydro-1Hpyrrol-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation 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.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 60846-91-5 ]

Aryls

Chemical Structure| 223407-18-9

A141655 [223407-18-9]

(R)-Benzyl (2-oxopyrrolidin-3-yl)carbamate

Similarity: 0.97

Chemical Structure| 1219424-59-5

A446509 [1219424-59-5]

Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate

Similarity: 0.92

Chemical Structure| 33628-84-1

A155970 [33628-84-1]

Methyl Z-L-Alaninamide

Similarity: 0.88

Chemical Structure| 879275-77-1

A376227 [879275-77-1]

(R)-3-N-Cbz-Aminopyrrolidine

Similarity: 0.84

Chemical Structure| 2766-17-8

A120188 [2766-17-8]

Z-Val-Gly-OEt

Similarity: 0.83

Amides

Chemical Structure| 223407-18-9

A141655 [223407-18-9]

(R)-Benzyl (2-oxopyrrolidin-3-yl)carbamate

Similarity: 0.97

Chemical Structure| 1219424-59-5

A446509 [1219424-59-5]

Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate

Similarity: 0.92

Chemical Structure| 33628-84-1

A155970 [33628-84-1]

Methyl Z-L-Alaninamide

Similarity: 0.88

Chemical Structure| 879275-77-1

A376227 [879275-77-1]

(R)-3-N-Cbz-Aminopyrrolidine

Similarity: 0.84

Chemical Structure| 2766-17-8

A120188 [2766-17-8]

Z-Val-Gly-OEt

Similarity: 0.83

Amines

Chemical Structure| 223407-18-9

A141655 [223407-18-9]

(R)-Benzyl (2-oxopyrrolidin-3-yl)carbamate

Similarity: 0.97

Chemical Structure| 1219424-59-5

A446509 [1219424-59-5]

Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate

Similarity: 0.92

Chemical Structure| 33628-84-1

A155970 [33628-84-1]

Methyl Z-L-Alaninamide

Similarity: 0.88

Chemical Structure| 879275-77-1

A376227 [879275-77-1]

(R)-3-N-Cbz-Aminopyrrolidine

Similarity: 0.84

Chemical Structure| 1217631-74-7

A105115 [1217631-74-7]

(S)-Benzyl pyrrolidin-3-ylcarbamate hydrochloride

Similarity: 0.82

Related Parent Nucleus of
[ 60846-91-5 ]

Pyrrolidines

Chemical Structure| 223407-18-9

A141655 [223407-18-9]

(R)-Benzyl (2-oxopyrrolidin-3-yl)carbamate

Similarity: 0.97

Chemical Structure| 1219424-59-5

A446509 [1219424-59-5]

Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate

Similarity: 0.92

Chemical Structure| 879275-77-1

A376227 [879275-77-1]

(R)-3-N-Cbz-Aminopyrrolidine

Similarity: 0.84

Chemical Structure| 1217631-74-7

A105115 [1217631-74-7]

(S)-Benzyl pyrrolidin-3-ylcarbamate hydrochloride

Similarity: 0.82

Chemical Structure| 1217652-74-8

A216700 [1217652-74-8]

(R)-Benzyl (pyrrolidin-2-ylmethyl)carbamate hydrochloride

Similarity: 0.80