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Chemical Structure| 3303-84-2 Chemical Structure| 3303-84-2

Structure of Boc-β-Ala-OH
CAS No.: 3303-84-2

Chemical Structure| 3303-84-2

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Synonyms: Boc-β-Ala-OH

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Product Details of [ 3303-84-2 ]

CAS No. :3303-84-2
Formula : C8H15NO4
M.W : 189.21
SMILES Code : O=C(O)CCNC(OC(C)(C)C)=O
Synonyms :
Boc-β-Ala-OH
MDL No. :MFCD00037291
InChI Key :WCFJUSRQHZPVKY-UHFFFAOYSA-N
Pubchem ID :76809

Safety of [ 3303-84-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 3303-84-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 0
Fraction Csp3 0.75
Num. rotatable bonds 6
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 46.86
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

75.63 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.66
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

0.43
Log Po/w (WLOGP)?

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

0.99
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.

0.51
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

0.01
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.72

Water Solubility

Log S (ESOL):?

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

-0.89
Solubility 24.5 mg/ml ; 0.129 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.

-1.59
Solubility 4.91 mg/ml ; 0.026 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

-1.02
Solubility 18.2 mg/ml ; 0.0962 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.

-7.15 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

1.0
Bioavailability Score?

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

0.56

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

0.0 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)

2.1

Application In Synthesis of [ 3303-84-2 ]

* 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 [ 3303-84-2 ]

[ 3303-84-2 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 3303-84-2 ]
  • [ 16947-84-5 ]
  • [ 174774-65-3 ]
  • (S)-2-Amino-3-{3-[(5-carbamimidoyl-benzofuran-2-carbonyl)-amino]-propionylamino}-propionic acid [ No CAS ]
  • 2
  • [ 3303-84-2 ]
  • [ 17664-93-6 ]
  • [ 223270-78-8 ]
  • 3
  • [ 22600-30-2 ]
  • [ 3303-84-2 ]
  • [ 547762-26-5 ]
  • 4
  • [ 3303-84-2 ]
  • [ 2886-33-1 ]
  • C26H32N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; sodium hydroxide; isobutyl chloroformate; In tetrahydrofuran; water; at -25 - 20℃; for 3h; Example 18: 2,3-Dihydrouridine-5'-carboxylic acid [(asparto)carbamoylethyl]-amide In a dry vessel, N-tert-butyloxycarbonyl-beta-alanine (10 mmol, 1890 mg) is dissolved in 10 ml of dry THF and cooled to -25 C. Subsequently, N-methylmorpholine (10 mmol, 1010 mg) and isobutyl chloroformiate (10 mmol, 1360 mg) are sequentially added under vigorous stirring. Immediately after the formation of a white precipitate (N-methylmorpholine hydrochloride) a solution of L-aspartic acid dibenzyl ester p-toluene sulfonate (11 mmol, 5330 mg) in 1 M-aq. NaOH-solution (11 ml) is added. The resulting mixture is allowed to warm to ambient temperature. After three hours, THF and other volatiles are removed by rotary evaporation at 40 C, the residual aqueous mixture is diluted with a small volume of H2O and adjusted to pH 1 (10% aq. NaHSO4 solution) and extracted with ethyl acetate (3 x 50 ml). The combined organic layers are washed with satured aq. Na2CO3 solution (3 x 20 ml) and subsequently with water (3 x 20 ml), dried over Na2SO4, and evaporated to dryness.
  • 5
  • [ 3303-84-2 ]
  • [ 97682-44-5 ]
  • [ 1094061-90-1 ]
  • 6
  • [ 3303-84-2 ]
  • [ 124-41-4 ]
  • [ 3034-48-8 ]
  • [ 1235447-14-9 ]
  • 7
  • [ 3325-11-9 ]
  • [ 3303-84-2 ]
  • [ 1246640-01-6 ]
YieldReaction ConditionsOperation in experiment
93% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 16h; 2.7 g (20 mmol) of <strong>[3325-11-9]5-aminobenzotriazole</strong>, 3.8 g (20 mmol) of 3-tert-butoxycarbonylaminopropionic acid, 3.5 g of HOBt (26 mmol) and 4.2 g (22 mmol) of DAPECI are dissolved in 30 ml of DMF and stirred at RT for 16 h. The reaction mixture is then evaporated in vacuo. The residue is taken up in 200 ml of ethyl acetate and washed by shaking twice with water. The organic phase is dried using MgSO4 and evaporated in vacuo. Purification by column chromatography on silica gel with ethyl acetate gives 5.7 g (93percent) of 28.
  • 8
  • [ 3303-84-2 ]
  • [ 23357-46-2 ]
  • C18H26N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; To 2.00 g of (R)-1-amino-1,2,3,4-tetrahydronaphthalene (13.6 mmol) in 20 ml of DMF was added 2.58 g of N-tBOC-β-alanine (13.6 mmol), 14 ml of Et3N (140 mmol), 1.84 g of HOBt (13.6 mmol), and 3.90 g of EDAC*HCl (10.2 mmol), and the mixture was stirred overnight at room temperature. Water and CH2Cl2 were added and separated, the water was rinsed several times with CH2Cl2, andthe combined CH2Cl2 layers were rinsed several times with brine before drying (MgSO4), filtering, and concentration. Chromatography with 25%-50% EtOAc in hexane yielded 3.58 g of product as a white solid (83%).
83% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; To 2.00 g of(R)-i-amino-i,2,3,4-tetrahydronaphthalene (13.6 mmol) in 20 mL of DMF was added 2.58 g of N-tBOC-13-alanine (13.6 mmol), 14 mL of Et3N (140 mmol), 1.84 g of HOBt (13.6 mmol) and 3.90 g of EDAC HC1 (10.2 mmol) and the mixture was stirred overnight at room temperature. Water and CH2C12 were added and separated, the water was rinsed several times with CH2C12, the combined CH2C12 layers were rinsed several times with brine beforedrying (MgSO4), filtering, and concentration, chasing the residual DMF off with toluene.Chromatography with 25-50% EtOAc in hexane yielded 3.58 g of product as a white solid(83%). ‘H NMR (300 MHz, CDC13) ö 7,20-7,25 (m, 1H), 7.17 (t, J= 3.5, 2H), 7.08-7.12 (m,1H), 5.91 (d, J= 6.5, 1H), 5.19 (t, J= 6.8, 2H), 3.43 (q, J= 6.1, 2H), 2.89 -2.67 (m, 2H), 2.42(t, J= 5.9, 2H), 2.10- 1.97 (m, 1H), 1.90- 1.77 (m, 3H), 1.42 (s, 9H). ‘3C NMR (75 MHz,CDC13) ö 170.54, 156.04, 137.50, 136.56, 129.14, 128.55, 127.27, 126.25, 79.25, 47.42, 36.93,36.45, 30.17, 29.18, 28.38, 19.97.
  • 9
  • [ 6972-82-3 ]
  • [ 3303-84-2 ]
  • tert-butyl 2-(3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)ethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of 5,6-diamino- 1 -methylpyrimidine-2,4( 1H,3H)-dione (1.56 g, 10.0 mmol), 3-(tert-butoxycarbonylamino)propanoic acid (3.78 g, 20.0 mmol), EDCI (3.83 g, 20.0 mmol) and DMAP (2.44 g, 20.0 mmol) in DMSO (40 mL) was stirred for 16 h at 28 °C. The reaction mixture was poured into water (250 mL) and the precipitate was collected. The above crude product and NaOH aqueous (10 mL, 3M) in MeOH (30 mL) was heated to reflux and stirred for 6 h. The reaction mixture was cooled to 28 °C and mixture was concentrated. The aqueous residue was neutralized with citric acid to PH = 67. The precipitate was collected and dried in vacuo to afford the title compound; ESI: 310.1 (M+H)t
  • 10
  • [ 6972-82-3 ]
  • [ 3303-84-2 ]
  • tert-butyl 2-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)ethylcarbamate [ No CAS ]
  • 11
  • [ 20876-36-2 ]
  • [ 3303-84-2 ]
  • 3-((tert-butoxycarbonyl)amino)-N-(2-oxo-2,3-dihydro-1H-indol-5-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% tert-butyl (3-oxo-3-((2-oxoindolin-5-yl)amino)propyl)carbamate (3b). To a solution of N-Boc amine 1 b (578.34 mg, 3.06 mmol), in dry DMF (5 ml_), under N2 atmosphere and cooled to 0°C, were added TBTU (982.54 mg, 3.06 mmol) and DIPEA (1 .07 ml_, 6.12 mmol). After 30' a 0°C, the amine salt 2b (0.58 mmol) was added and the temperature was kept at 0°C for additional 30'. Later the mixture was slowly warmed to rt and left under stirring at rt overnight. Once TLC verified the disappearance of the precursor, the organic solvent was evaporated under vacuum and the crude product was purified by flash chromatography over silica gel, using CHC /MeOH (95:5) as the eluent, to obtain pure 3b as a white solid (806 mg, 2.53 mmol, 83percent yield). H-NMR (DMSO-c/6): delta 1 .39 (s, 9H, Boc); 2.42 (t, 2H, J = 7.2 Hz, CH2); 3.1 6-3.22 (m, 2H, CH2); 3.45 (s, 2H, CH2); 6.71 (d, 1 H, J = 8.4 Hz, Ar); 6.84-6.88 (br t, 1 H, J = 5.6 Hz, NH); 7.32 (dd, 1 H, J = 1 .6, 8.4 Hz); 7.50 (s, 1 H, Ar); 9.78 (br s, 1 H, NH); 10.28 (br s, 1 H, NH) ppm. Anal. Calcd for C16H21 N3O4: C, 60.37percent; H, 6.33percent; N, 13.20percent; Found: C, 60.17percent; H, 6.23percent; N, 13.22percent.
  • 12
  • [ 3303-84-2 ]
  • [ 1022641-52-6 ]
  • tert-butyl (3-((6-bromopyridin-3-yl)(methyl)amino)-3-oxopropyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃; for 16h; To a stirred solution of the compound obtained in the previous section, step b, (450 mg, 2.41 mmol) and 3-(tertbutoxycarbonylamino)propanoic acid (457 mg, 2.41 mmol) in DCM (10 ml) was added EhN (1.7 ml, 12.0920 mmol) and T3P (2.3 g, 7.25 mmol) at RT. The reaction mixture was stirred at RT for 16h. The reaction mixturewas diluted with DCM (20 ml) and water (20 ml). Separated the organic layer, washed with water (20 ml),brine solution (10 ml) and dried over anhydrous Na2S04 and concentrated. The crude compound was purifiedby flash column chromatography and eluted at 50% EtOAc/Pet Ether to afford the title compound (0.3 g, 35%)as a white solid.25 LC-MS (method 1 ): Rt = 1.86 min; m/z = 358.20 (M+H+).
35% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃; for 16h; To a stirred solution of the compound obtained in the previous section, step b, (450 mg, 2.41 mmol) and 3-(tert- butoxycarbonylamino) propanoic acid (457 mg, 2.41 mmol) in DCM (10 mL) was added EN (1.7 mL, 12.09 mmol) and T3P (2.3 g, 7.25 mmol) at RT. The reaction mixture was stirred at RT for 16h. The reaction mixture was diluted with DCM (20 mL) and water (20 mL). Separated the organic layer, washed with water (20 mL), brine solution (10 mL) and dried over anhydrous NajSC and concentrated. The crude compound was purified by flash column chromatography and eluted at 50% EtOAc/Pet Ether to afford the title compound (0.3 g, 35%) as a white solid. (0653) LC-MS (method 1); Rt = 1.86 min; m/z = 358.20 (M+H~).
  • 13
  • [ 3303-84-2 ]
  • [ 39987-25-2 ]
  • C9H16N2O5 [ No CAS ]
  • 14
  • [ 25519-82-8 ]
  • [ 3303-84-2 ]
  • tert-butyl 3-(4-(4-methoxybenzoyl)piperidin-1-yl)-3-oxopropylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
735 mg With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 12h; General procedure: 3- (tert-Butoxycarbonylamino) propionic acid (555 mg, 2.932 mmol) obtained in Step 1,PyBOP (1.525 g, 2.932 mmol),(4-methoxyphenyl) (piperidin-4-yl) methanone hydrochloride(500 mg, 1.955 mmol)To DMF After dissolution, DIPEA (1.02 ml, 5.865 mmol)And the mixture was stirred at room temperature for 12 hours.The reaction solution was diluted with ethyl acetate and washed three times with water.The organic layer was dehydrated with Na2SO4,After concentration under reduced pressure, the product was separated by column chromatography to obtain 735 mg of the titled compound as a yellow liquid.
  • 15
  • [ 854601-60-8 ]
  • [ 3303-84-2 ]
  • C26H54N2O12 [ No CAS ]
 

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