138326-68-8|(S)-Methyl 2-amino-2-cyclopropylacetate hydrochloride| Ambeed

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Quality Control of [ 138326-68-8 ] Purity: 97% SDS Specification

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Product Details of [ 138326-68-8 ]

CAS No. :	138326-68-8
Formula :	C₆H₁₂ClNO₂
M.W :	165.62
SMILES Code :	O=C(OC)[C@@H](N)C1CC1.[H]Cl
MDL No. :	MFCD09607984
InChI Key :	SRMSADQSMWKRRW-JEDNCBNOSA-N
Pubchem ID :	42614509

Safety of [ 138326-68-8 ]

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

Computational Chemistry of [ 138326-68-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	0.83
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	39.8
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	0.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.64
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.	0.35
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	0.23
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.4

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.17
Solubility	11.3 mg/ml ; 0.0682 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.	-1.47
Solubility	5.62 mg/ml ; 0.0339 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	-0.21
Solubility	103.0 mg/ml ; 0.621 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	Yes
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.	-6.75 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.	0.55

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	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)	1.73

Application In Synthesis of [ 138326-68-8 ]

* 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 [ 138326-68-8 ]

[ 138326-68-8 ] Synthesis Path-Downstream 1~31

1
[ 67-56-1 ]
[ 49606-99-7 ]
[ 138326-68-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	With thionyl chloride; at 0 - 20℃; for 4.0h;Heating / reflux;	To a 0 C. solution of thionyl chloride (7.6 mL, 104 mmol) in anhydrous methanol (750 mL) was added (S)-cyclopropylglycine (10.0 g, 86.9 mmol, Eastman Chemical Company, Kingsport, Tenn.). The reaction mixture was allowed to warm to room temperature and then refluxed for 4 hrs, then cooled to room temperature and concentrated in vacuo to give a crude solid. The solids were washed with acetone to give 8.94 g of the product as a white solid. Yield: 62%, MS: 130 (M+H+), mp=134.0-135.9 C.
62%	With thionyl chloride; In methanol; at 0 - 20℃; for 4.0h;Heating / reflux;	To a 0 C. solution of thionyl chloride (7.6 mL, 104 mmol) in anhydrous methanol (750 mL) was added (S)-cyclopropylglycine (10.0 g, 86.9 mmol, Eastman Chemical Company, Kingsport, Tenn.). The reaction mixture was allowed to warm to room temperature and then refluxed for 4 hrs, then cooled to room temperature and concentrated in vacuo to give a crude solid. The solids were washed with acetone to give 8.94 g of (S)-cyclopropylglycine methyl ester HCl as a white solid. Yield: 62%, MS: 130 (M+H+), mp=134.0-135.9 C.
	With acetyl chloride; at 0 - 20℃;	To a suspension of H-Cpg-OH (LS3-A, 20.0 g, 174 mmol, 1.0 eq) in anhydrous MeOH (350 mL) at 0 C. was slowly added freshly distilled (from PCl5) acetyl chloride (185 mL, 2.6 mol, 15 eq) over 45 min. The mixture was allowed to warm to room temperature and stirred 16-18 h. The reaction was monitored by TLC [MeOH/NH4OH/AcOEt (10:2:88); detection: ninhydrin; Rf=0.50]. The mixture was then concentrated under vacuum, azeotroped with toluene (3*) and dried under high vacuum 16-18 h to give LS3-1 as a pale yellow solid (30.0 g, >100% crude yield). 1H NMR (CD3OD): delta 4.88 (3H, s, NH3+), 3.85 (3H, s, CH3O), 3.36-3.33 (1H, d, NH3+CHCH3O), 1.19-1.10 (1H, m, CH(CH2)2), 0.83-0.53 (4H, m, CH(CH2)2).

References: [1]Patent: US2004/77646,2004,A1 .Location in patent: Page 88.
[2]Patent: US2004/248949,2004,A1 .Location in patent: Page 33.
[3]Journal of the American Chemical Society,2015,vol. 137,p. 2042 - 2046.
[4]Patent: US2018/110824,2018,A1 .Location in patent: Paragraph 0642; 0643; 0644.

2
[ 138326-68-8 ]
L-α-cyclopropylglycinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonia; In methanol; at 0 - 70℃; for 48.0h;	To a 0 C. solution of ammonia in methanol (100 ML, 7M) in a bomb was added (S)-cyclopropylglycine ethyl ester HCl (5.04 g, 30.4 mmol).The bomb was sealed and placed in a 70 C. oil bath for two days.The reaction mixture was cooled to room temperature and concentrated until a suspension formed.The suspension was filtered and the collected solids were washed with methanol:acetone (1:1).Another crop of solids was obtained from the mother liquor in this manner, and the combined solids were dried to give 3.52 g of the product as a white powder. Yield: 100%, MS: 115 (M+H+), mp=225.0-231.0 C., [alpha]D25=+63.0 (1.00, 1M HCl).
100%	With ammonia; In methanol; at 0 - 70℃; for 48.0h;	To a 0 C. solution of ammonia in methanol (100 mL, 7M) in a bomb was added (S)-cyclopropylglycine methyl ester HCl (5.04 g, 30.4 mmol). The bomb was sealed and placed in a 70 C. oil bath for two days. The reaction mixture was cooled to room temperature and concentrated until a suspension formed. The suspension was filtered and the collected solids were washed with methanol:acetone (1:1). Another crop of solids was obtained from the mother liquor in this manner, and the combined solids were dried to give 3.52 g of the product as a white powder. Yield: 100%, MS: 115 (M+H+), mp=225.0-231.0 C., [alpha]D25=+63.0 (1.00, 1M HCl).

References: [1]Patent: US2004/77646,2004,A1 .Location in patent: Page 88.
[2]Patent: US2004/248949,2004,A1 .Location in patent: Page 33.

4
[ 77-76-9 ]
[ 155976-13-9 ]
[ 138326-68-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride; In water; at 40℃;	Synthesis of (S)-amino-cvclopropyl-acetic acid methyl ester (4) . A solution of Boc-L-cyclopropylglycine (97 mg, 0.45 mmol) and HCl(cone, 500 mul) in 2,2-dimethoxypropane (5 ml, 40 mmol) was maintained at 40 C overnight. Reaction mixture was evaporated in vacuum. Residue was dissolved in i-PrOH (10 ml) and evaporated in vacuum. The aforementioned procedure was repeated twice. Residue was triturated with ether, filtrated, washed with ether and dried in vacuum overnight to obtained hydrochloric salt of target product (4) (73 mg, 98%) as off-white powder. LC-MS [M+H] 130.0 (C6H11NO2+H, requires 130.17).

References: [1]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 213.

5
[ 138326-68-8 ]
[ 1093191-34-4 ]
[ 1093191-55-9 ]

Yield	Reaction Conditions	Operation in experiment
65%		Synthesis of (S)-cyclopropyl-[4-(4-morpholin-4-ylmethyl-phenylethynyl)-benzoylamino]- acetic acid methyl ester (5). A solution of compound (3) hydrochloride (143 mg, 0.4 mmol), HATU (176 mg, 0.44 mmol) and DIEA (313 mul, 1.8 mmol) in DMF (1 ml) was maintained at ambient temperature for 10 min followed by the addition of compound (4) hydrochloride (73 mg, 0.44 mmol). Reaction mixture was stirred at ambient temperature overnight, diluted with EtOAc (80 ml) and extracted with water (20 ml x 2) and brine (20 ml). Organic layer was dried over anh. MgSO4 and evaporated in vacuum. Residue was dissolved in DCM (1 ml) and subjected to flash chromatography on CombiFlash Companion unit equipped with RediSep flash column (normal phase, 35-60 micron average particle size silicagel, 4g, Teledyne Isco); flow rate = 18 ml/min; injection volume 1.5 ml; mobile phase A: DCM; mobile phase B: MeOH; gradient 0-30%B in 38 min. Fractions containing the desired product were combined and concentrated in vacuum. Residue was dried in vacuum overnight to obtaine target product 5 (112 mg, 65%) as off-white powder. LC-MS [M+H] 433.2 (C26H28N2O4+H, requires 433.53).

References: [1]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 213-214.

6
[ 138326-68-8 ]
[ 1047665-89-3 ]
[ 1047665-90-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 105℃;	A slightly modified reaction sequence to that described for compounds 801 and 807 can also be employed to assemble the macrocyclic framework. In this approach, the initial alkylation as done via an SN2 displacement rather than a Mitsunobu reraction. This is illustrated for the synthesis of compound 877 from the bromide derived from tether Boc-T75a (M13), cyclopropylglycine methyl ester (M14) and the protected dipeptide (M20) in an overall yield of 35%.

References: [1]Patent: US2008/194672,2008,A1 .Location in patent: Page/Page column 62.

7
[ 138326-68-8 ]
[ 693213-58-0 ]

Yield	Reaction Conditions	Operation in experiment
19.1 g	With sodium carbonate; In water;	The hydrochloride salt LS3-1 was dissolved in an aqueous solution of Na2CO3 (1 M, 275 mE, 0.272 mol, 1.5 eq). The basic aqueous phase was saturated with NaC1 and extracted with AcOEt/CH2C12 (2:1) (5x1.00 mE). TEC [MeOH/NH4OH/AcOEt (10:2:88); detection: ninhydrin; R1=0.50]. The combined organic phases were dried over Mg504, filtered and concentrated under low vacuum at room temperature to give free amino-ester E53-3 as a yellow oil (19.1 g, 85%, 2 steps). E53-3is volatile and should not be lefi on a mechanical vacuum pump for extended periods of time. To minimize diketopiperazine formation, Step E53-4 should occur immediately after isolation of E53-3. ?H NMR (CDC13): oe 3.70 (3H, s, C130), 2.88-2.85(1H, d, NH2CHCH3O), 1.54 (1H, s, NH2), 1.04-0.97 (1H, m,CH(CH2)2), 0.56-0.27 (4H, m, CH(C)2).

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.
[2]Patent: US2018/110824,2018,A1 .Location in patent: Paragraph 0642; 0649; 0650.

8
[ 138326-68-8 ]
[ 874336-34-2 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.
[2]Patent: US2018/110824,2018,A1 .

9
[ 138326-68-8 ]
[ 874336-36-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.
[2]Patent: US2018/110824,2018,A1 .

10
[ 138326-68-8 ]
[ 874336-40-0 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.

11
[ 138326-68-8 ]
[ 1351469-17-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.

12
[ 138326-68-8 ]
[ 874336-42-2 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.
[2]Patent: US2018/110824,2018,A1 .

13
[ 138326-68-8 ]
[ 874336-35-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.
[2]Patent: US2018/110824,2018,A1 .

14
[ 138326-68-8 ]
[ 874336-43-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.
[2]Patent: US2018/110824,2018,A1 .

15
[ 138326-68-8 ]
ulimorelin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.
[2]Patent: US2018/110824,2018,A1 .

16
[ 49606-99-7 ]
[ 75-36-5 ]
[ 138326-68-8 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.

17
[ 138326-68-8 ]
[ 358-23-6 ]
(S)-methyl 2-cyclopropyl-2-(trifluoromethylsulfonamido)acetate [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 2042 - 2046.

18
[ 138326-68-8 ]
(-)-(2S)-methyl 2-(2-(p-tolyl)cyclopropyl)-2-(trifluoromethylsulfonamido)acetate [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 2042 - 2046.

19
[ 138326-68-8 ]
(-)-(2S)-methyl 2-(2-(p-tolyl)cyclopropyl)-2-(trifluoromethylsulfonamido)acetate [ No CAS ]
(2S)-methyl 2-(2-(p-tolyl)cyclopropyl)-2-(trifluoromethylsulfonamido)acetate [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 2042 - 2046.

20
[ 138326-68-8 ]
(2S)-methyl 2-(2-(p-tolyl)cyclopropyl)-2-(trifluoromethylsulfonamido)acetate [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 2042 - 2046.

21
[ 138326-68-8 ]
C₅₀H₆₁FN₄O₉*ClH [ No CAS ]

References: [1]Patent: US2018/110824,2018,A1 .

22
[ 138326-68-8 ]
C₃₅H₄₉FN₄O₇*ClH [ No CAS ]

References: [1]Patent: US2018/110824,2018,A1 .

23
[ 138326-68-8 ]
[ 1093191-34-4 ]
[ 1093191-57-1 ]

References: [1]Patent: WO2008/154642,2008,A2 .

24
[ 138326-68-8 ]
C₂₁H₂₇N₃O₄ [ No CAS ]