[ CAS No. 1212257-18-5 ] {[proInfo.proName]}

Name: 1212257-18-5|Fmoc-L-Cyclopropylglycine|95%
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Quality Control of [ 1212257-18-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1212257-18-5 ]

SDS Specification

Alternatived Products of [ 1212257-18-5 ]

Product Details of [ 1212257-18-5 ]

CAS No. :	1212257-18-5	MDL No. :	MFCD06659145
Formula :	C₂₀H₁₉NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YMLZBPTXRMNAFP-SFHVURJKSA-N
M.W :	337.37	Pubchem ID :	2761462
Synonyms :

Calculated chemistry of [ 1212257-18-5 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.3
Num. rotatable bonds :	7
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	92.67
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	3.43
Log Po/w (WLOGP) :	3.33
Log Po/w (MLOGP) :	2.78
Log Po/w (SILICOS-IT) :	3.01
Consensus Log Po/w :	2.92

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.99
Solubility :	0.0349 mg/ml ; 0.000103 mol/l
Class :	Soluble
Log S (Ali) :	-4.7
Solubility :	0.00675 mg/ml ; 0.00002 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.09
Solubility :	0.00273 mg/ml ; 0.00000809 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.69

Safety of [ 1212257-18-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1212257-18-5 ]

* 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.

Upstream synthesis route of [ 1212257-18-5 ]
Downstream synthetic route of [ 1212257-18-5 ]

[ 1212257-18-5 ] Synthesis Path-Upstream 1~1

1
[ 28920-43-6 ]
[ 49606-99-7 ]
[ 1212257-18-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium carbonate In 1,4-dioxane; water at 0 - 25℃; for 8.17 h;	(5)-2-((((9/ -fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (43a): To a stirred solution of Na2C03 (2.3 g) in water (34 mL) was added (2C1₂); FT-IR (neat) 2669, 2335, 2159, 2106, 1785, 1689, 1550, 1489, 1463, 1433, 1369, 1296, 1253, 1172, 1128, 1001 cm^"1; NMR: (CDCI₃, 600 MHz) δ = 7.76 (d, 2 H, J = 7.2 Hz), 7.60-7.59 (m, 2 H), 7.41-7.39 (m, 2 H), 7.32-7.30 (m, 2 H), 5.36 (d, 1 H, J = 6), 4.45-4.39 (m, 2 H), 4.24-4.21 (m, 1 H), 3.83-3.81 (m, 1 H), 1.14-1.13 (m, 1 H), 0.65-0.46 (m, 5 H) ppm. ¹³C NMR: (CDCI₃, 150 MHz) δ = 176.6, 156.2, 143.9, 143.8, 141.4, 127.9, 127.2, 125.2, 125.1, 120.1, 67.3, 57.4, 47.3, 13.9, 3.4 ppm; HRMS calcd for C20H19NO4 [ +Na⁺] 360.1206 found 360.1193.

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 5, p. 1698 - 1708
[2] Patent: WO2016/138288, 2016, A1, . Location in patent: Page/Page column 124

[ 1212257-18-5 ] Synthesis Path-Downstream 1~40

1
[ 1212257-18-5 ]
C₂₀H₁₉NO₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2136 - 2160

2
[ 1212257-18-5 ]
C₂₇H₃₄N₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2136 - 2160

3
[ 1212257-18-5 ]
[ 6638-79-5 ]
C₂₂H₂₄N₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2136 - 2160

4
[ 28920-43-6 ]
[ 49606-99-7 ]
[ 1212257-18-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium carbonate; In 1,4-dioxane; water; at 0 - 25℃; for 8.17h;	(5)-2-((((9/ -fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (43a): To a stirred solution of Na2C03 (2.3 g) in water (34 mL) was added (<S)-2-amino-2-cyclopropylacetic acid (1.0 g, 8.68 mmol). The resulted solution was cooled to 0 C and 1,4-dioxane (21.7 mL) was added dropwise at the same temperature. A solution of Fmoc-Cl (2.48 g, 9.59 mmol) in dioxane (21.7 mL) was added dropwise to the above reaction mixture over 10 min at 0 C. The reaction mixture was stirred at 0 C for 2 h followed by 6 h at 25 C. The solvent was evaporated under reduced pressure and the resulted residue was dissolved in water (150 mL). The aqueous layer was extracted with EtOAc (4 x 150 mL). The aqueous layer was then acidified with {M) HC1 to pH 2 and extracted with EtOAc (4 x 100 mL). The resulted organic layers were combined and washed with brine (100 mL), dried over Na2S04, and evaporated to give a white solid. The solid was stirred with hexane (60 mL) for 1 h and then hexane was decanted. The white solid was dissolved in boiling ethyl acetate (50 mL). Then hexane (100 mL) was added dropwise to the above solution while warming gently. The solution was allowed to cool to room temperature and then kept at 0 C for crystallization. The crystallized white solid was isolated by filtration, washed with hexane (2 x 50 mL), and vacuum dried to give 43a as a white solid (2.45 g, 84% yield). 43a: [alpha] = +15.7 (c 1.0, CH2C12); FT-IR (neat) 2669, 2335, 2159, 2106, 1785, 1689, 1550, 1489, 1463, 1433, 1369, 1296, 1253, 1172, 1128, 1001 cm"1; NMR: (CDCI3, 600 MHz) delta = 7.76 (d, 2 H, J = 7.2 Hz), 7.60-7.59 (m, 2 H), 7.41-7.39 (m, 2 H), 7.32-7.30 (m, 2 H), 5.36 (d, 1 H, J = 6), 4.45-4.39 (m, 2 H), 4.24-4.21 (m, 1 H), 3.83-3.81 (m, 1 H), 1.14-1.13 (m, 1 H), 0.65-0.46 (m, 5 H) ppm. 13C NMR: (CDCI3, 150 MHz) delta = 176.6, 156.2, 143.9, 143.8, 141.4, 127.9, 127.2, 125.2, 125.1, 120.1, 67.3, 57.4, 47.3, 13.9, 3.4 ppm; HRMS calcd for C20H19NO4 [ +Na+] 360.1206 found 360.1193.

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708
[2]Patent: WO2016/138288,2016,A1 .Location in patent: Page/Page column 124

5
[ 1212257-18-5 ]
(9H-fluoren-9-yl)methyl (S)-(1-cyclopropyl-2-fluoro-2-oxoethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine; diethylamino-sulfur trifluoride; In dichloromethane; at 25℃; for 1h;	(9/ -fluoren-9-yl)methyl (£)-(l-cyclopropyl-2-fluoro-2-oxoethyl)carbamate (43): To a stirred solution of 43a (0.2 g, 0.59 mmol) and pyridine (0.048 mL, 0.59 mmol) in CH2C12 (3.55 mL) was added a solution of (diethylamino)sulfur trifluride (0.095 mL, 0.71 mmol) in CH2C12 (0.6 mL) dropwise at 25 C. The reaction mixture was stirred for 1 h at 25 C and then diluted with CH2CI2 (30 mL). The solution was washed with ice-cold water (2 x 20 mL), dried over Na2SC>4, concentrated, and recrystallized from CH2Cl2/hexanes to furnish the acyl fluoride 43 (0.17 g, 85% yield) as white solid. 43: [a]22 = +13.5 (c 1.0, CH2C12); FT-IR (neat) ?fKSs;;s 2668, 2345, 2109, 1775, 1627, 1581, 1482, 1364, 1213, 1132, 1001 cm"1; NMR: (CDCI3, 600 MHz) delta = 7.78 (d, 2 H, J = 7.2 Hz), 7.60-7.58 (m, 2 H), 7.43-7.40 (m, 2 H), 7.33 (t, 2 H, J = 7.2 Hz), 5.29- 5.28 (m, 1 H), 4.49-4.41 (m, 2 H), 4.23 (t, 1 H, J = 6.6 Hz), 3.86-3.83 (m, 1 H), 1.19-1.12 (m, 1 H), 0.76-0.48 (m, 5 H) ppm. 13C NMR: (CDC13, 150 MHz) delta = 162.16 (d, J = 370.5 Hz), 155.8, 143.7, 141.5, 127.9, 127.3, 125.1, 120.1, 67.5, 56.9 (d, J = 60 Hz), 47.2, 12.8, 3.8 (d, 7 = 28.5) ppm. HRMS data could not be obtained for this compound.

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708
[2]Patent: WO2016/138288,2016,A1 .Location in patent: Page/Page column 124-125

6
[ 1212257-18-5 ]
methyl (2S,4R)-4-(2-((5S,8R,10R)-5-cyclopropyl-1-(9H-fluoren-9-yl)-8-isopropyl-7-methyl-3,6,12-trioxo-2,11-dioxa-4,7-diazatridecan-10-yl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708
[2]Patent: WO2016/138288,2016,A1

7
[ 1212257-18-5 ]
C₃₁H₄₄N₄O₆S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708
[2]Patent: WO2016/138288,2016,A1

8
[ 1212257-18-5 ]
methyl (2S,4R)-4-(2-((1R,3R)-1-acetoxy-3-((S)-2-cyclopropyl-N-methyl-2-((R)-1-methylpiperidine-2-carboxamido)acetamido)-4-methylpentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 1698 - 1708
[2]Patent: WO2016/138288,2016,A1

9
[ 1212257-18-5 ]
methyl (2S,4R)-4-(2-((6S,9R,11R)-6-cyclopropyl-9-isopropyl-2,8-dimethyl-4,7,13-trioxo-12-oxa-2,5,8-triazatetradecan-11-yl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoate [ No CAS ]