Boc-Ser(Me)-OH | Carbamates

Structure of Boc-Ser(Me)-OH
CAS No.: 51293-47-1

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Quality Control of [ 51293-47-1 ] Purity: 97% SDS Specification

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Product Details of [ 51293-47-1 ]

CAS No. :	51293-47-1
Formula :	C₉H₁₇NO₅
M.W :	219.24
SMILES Code :	O=C(O)[C@@H](NC(OC(C)(C)C)=O)COC
MDL No. :	MFCD00153314

Safety of [ 51293-47-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 51293-47-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	0
Fraction Csp3	0.78
Num. rotatable bonds	7
Num. H-bond acceptors	5.0
Num. H-bond donors	2.0
Molar Refractivity	52.75
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.76
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.41
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.61
Log P_o/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.	0.01
Log P_o/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	-0.14
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.53

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.0
Solubility	22.1 mg/ml ; 0.101 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.	-1.76
Solubility	3.82 mg/ml ; 0.0174 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	-0.79
Solubility	35.2 mg/ml ; 0.161 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.	-7.35 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.	0.56

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)	2.97

Application In Synthesis of [ 51293-47-1 ]

* 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 [ 51293-47-1 ]

[ 51293-47-1 ] Synthesis Path-Downstream 1~54

1
[ 3262-72-4 ]
[ 74-88-4 ]
[ 51293-47-1 ]

Yield	Reaction Conditions	Operation in experiment
28%		A. (S)-2-(tert-Butoxycarbonylamino)-3-methoxypropanoic acid A sodium methanolate (NaOMe) solution was prepared by slowly adding MeOH (50 mL) to a suspension of sodium hydride (60percent in mineral oil, 28 g, 0.71 mol) in dry THF (1.2 L) at 0° C. The resulting mixture was stirred at RT for 2 h. A portion of the NaOMe solution (320 mL) was added to (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (36 g, 175 mmol) in dry THF (1.6 L), and the mixture was stirred at RT for 1 h. Methyl iodine (16 mL) was then added and the mixture was stirred at RT for 1 h. Another aliquot of NaOMe solution (540 mL) was added and the reaction mixture stirred at RT for 1 h. Additional methyl iodine (38 mL) in THF (200 mL) was added and the reaction mixture was stirred at RT for 36 h. Following reaction, the mixture was concentrated and the residue was dissolved in water and washed with diethyl ether (2.x.100 mL). The aqueous layer was acidified to pH 2 by the addition of solid citric acid and was extracted with EtOAc (3.x.200 mL) and dried over Na2SO4. The organic phase was concentrated, and the residue was dissolved in water and extracted with DCM (4.x.150 mL). The organic layers were combined and concentrated to give the title compound as an oil, which was used without further purification (10.9 g, 28percent).

References: [1]Patent: US2011/152273,2011,A1 .Location in patent: Page/Page column 87.
[2]Journal of Organic Chemistry,1979,vol. 44,p. 2299 - 2300.

2
2-(S)-amino-4-methyl-1-(5-phenyl-[1,3,4]oxadiazol-2-yl)-(R/S)-pentan-1-ol hydrochloride [ No CAS ]
[ 51293-47-1 ]
[ 660847-58-5 ]

Yield	Reaction Conditions	Operation in experiment
79%		[N-A-BOC-0-METHYL-L-SERINE] (2.19g, 10.0 mmol), HOBt (1.62g, 12.0 mmol), [1-ETHYL-3- (3APOS;-DIMETHYLAMINO-PROPYL) CARBODIIMIDE] hydrochloride (EDC, 2. [01G,] 10.5 mmol), and N-methylmorpholine (1.4 mL, 12.5 mmol) were stirred in 150 mL anhydrous dichloromethane. After 5 min, [2-AMINO-4-METHYL-L- (5-PHENYL-] [[1,] 3,4] oxadiazol-2-yl)-pentan-1-ol hydrochloride (2.61g, 10.0 mmol) dissolved in dichloromethane (50 [ML)] and more N-methylmorpholine (1.4 mL, 12.5 mmol) were added. After 3 hr, the reaction mixture was transferred to a separatory funnel and washed twice with 100 mL portions [OF 0. 5N] aqueous [HCI.] The organic phase was separated and once with water (50 mL) and twice with saturated aqueous sodium bicarbonate (100 mL). The organic phase was dried over anhydrous magnesium sulfate. Filtration and solvent evaporation gave a tan foam. This was flash chromatographed on silica gel, eluting with 5percent methanol in dichloromethane to give (1- 1- [hydroxy- (5-phenyl- [1, 3,4] oxadiazol-2-yl) methyl]-3-methyl-butylcarbamoyl}- 2-methoxyethyl) carbamic acid ter-butyl ester as a brittle, pale yellow foam, (3.65g, 79percent) as a mixture of diastereomers.

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2953 - 2968.
[2]Patent: WO2004/14882,2004,A2 .Location in patent: Page 37.

3
[ 1004316-18-0 ]
[ 51293-47-1 ]
[ 1004318-04-0 ]

References: [1]Patent: WO2008/10921,2008,A2 .Location in patent: Page/Page column 280.
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 995 - 999.

4
[ 107-19-7 ]
[ 51293-47-1 ]
N^α-(tert-butoxycarbonyl)-O-methyl-L-serine N-propargylamide [ No CAS ]

References: [1]Macromolecules,2005,vol. 38,p. 10605 - 10608.

5
[ 51293-47-1 ]
(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methoxy-propionylamino)-propionic acid [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2004,vol. 14,p. 239 - 243.

6
[ 51293-47-1 ]
{(S)-1-[(S)-1-((1S,2S,4R)-1-Benzyl-2-hydroxy-4-{(S)-2-methyl-1-[(pyridin-4-ylmethyl)-carbamoyl]-propylcarbamoyl}-pentylcarbamoyl)-ethylcarbamoyl]-2-methoxy-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2004,vol. 14,p. 239 - 243.

7
[ 51293-47-1 ]
[ 161561-66-6 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7671 - 7676.
[2]Tetrahedron Letters,1995,vol. 36,p. 67 - 70.

8
[ 51293-47-1 ]
(R)-2-(1-tert-Butoxycarbonylamino-vinyl)-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7671 - 7676.

9
[ 51293-47-1 ]
[ 183793-54-6 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7671 - 7676.

10
[ 51293-47-1 ]
[ 183793-55-7 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7671 - 7676.

11
[ 51293-47-1 ]
[ 183793-52-4 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7671 - 7676.

12
[ 51293-47-1 ]
[ 183793-53-5 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7671 - 7676.

13
[ 51293-47-1 ]
2-((R)-1-tert-Butoxycarbonylamino-2-methoxy-ethyl)-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7671 - 7676.

14
[ 51293-47-1 ]
[ 183904-76-9 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7671 - 7676.

15
[ 24424-99-5 ]
[ 51293-47-1 ]