[ CAS No. 36061-08-2 ]

Name: 36061-08-2|(R)-2-Amino-5-phenylpentanoic acid|98%
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SKU: A519211
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Quality Control of [ 36061-08-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 36061-08-2 ]

CAS No. :	36061-08-2	MDL No. :	MFCD03844654
Formula :	C₁₁H₁₅NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XOQZTHUXZWQXOK-SNVBAGLBSA-N
M.W :	193.24	Pubchem ID :	6993756
Synonyms :

Calculated chemistry of [ 36061-08-2 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	55.12
TPSA :	63.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.75
Log Po/w (XLOGP3) :	-0.36
Log Po/w (WLOGP) :	1.42
Log Po/w (MLOGP) :	-0.52
Log Po/w (SILICOS-IT) :	1.59
Consensus Log Po/w :	0.78

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.8
Solubility :	30.7 mg/ml ; 0.159 mol/l
Class :	Very soluble
Log S (Ali) :	-0.51
Solubility :	60.1 mg/ml ; 0.311 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.68
Solubility :	0.406 mg/ml ; 0.0021 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.77

Safety of [ 36061-08-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H312-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 36061-08-2 ]

* 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 [ 36061-08-2 ]

[ 36061-08-2 ] Synthesis Path-Downstream 1~11

1
[ 36061-08-2 ]
[ 64-17-5 ]
D-2-amino-5-phenylpentanoic acid ethyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogenchloride	4 Reflux was resumed the next morning for-1 hour and then 50 mLs of ethyl acetate was added to the vessel. The solution was then concentrated down to-30 mLs via atmospheric distillation. This sequence (i. e. addition of ethyl acetate followed by atmospheric concentration) was repeated twice more before a final addition of 30 mL of ethyl acetate to the warm mixture. The solution was cooled slowly to room temperature (over several hours) and the resulting slurry was stirred at room temperature for 40 minutes. Subsequent filtration and rinsing (once with 10 mLs of cold ethyl acetate), followed by vacuum drying at 50°C, yielded 2.47 grams (-92%) of the title compound. 'H nmr (DMSO-d6) : 8 1.15-1. 21 (t, 3H), 1.50-1. 89 (m, 4H), 2.48-2. 67 (m, 2H), 3.92- 3.98 (t, 1H), 4.08-4. 25 (m, 2H), 7.12-7. 29 (m, 5H), 8.76 (s, broad, 3H).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2003/87036, 2003, A1 Location in patent: Page/Page column 10

2
[ 108019-30-3 ]
[ 36061-08-2 ]

Yield	Reaction Conditions	Operation in experiment
47.29%	With hydrogenchloride; potassium hydroxide; water at 40℃; for 12h;	3 A solution consisting of (DL)-N-acetyl-2-amino-5-phenylpentanoic acid (10.0 grams, 0.043 moles), zinc chloride (0.003 grams), 2 N potassium hydroxide solution (21.5 mL, 0.043 moles), and water (128.5 mL) was adjusted to a pH of 8.0 by the addition concentrated hydrochloric acid. To the reaction mixture was added D-aminoacylase (N- Acyl-D-amino acid amidohydrolase, 0.1 grams) which was then vigorously stirred for 12 hours at 40 °C while maintaining a pH of 8.0 by the addition of 2N potassium hydroxide and concentrated hydrochloric acid. The product was isolated by filtration, washed with heptane (20 mL) and dried in vacuum at 50 ° C to give 3.89 grams (47.29%) of the above-identified product, (D)-N-amino-5-phenylpentanoic acid :'H nmr (TFA-D) : 8 1.906-1. 942 (m, 2H), 2.134-2. 192 (m, 2H), 2.74-2. 786 (m, 2H), 4.352-4. 373 (m, 1H), 7.161-7. 320 (m, 5H), 11.601 (s, 6H).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2003/87036, 2003, A1 Location in patent: Page/Page column 9-10

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol at 25℃; for 2h; Stage #2: With trifluoroacetic acid In dichloromethane at 25℃; for 1h;	2 Synthesis of 2-amino-5-phenylvaleric acid General procedure: Under nitrogen, add iodobenzene (2.04g, 10mmol), N-tert-butoxycarbonyl-propargylglycine (2.13g, 10mmol), CuCl (0.04g, 0.40mmol), and dissolve in 40mL of tetrahydropyrrole,Then Pd(PPh3)2Cl2 (0.14g, 0.2mmol) was added, and the reaction was stirred at room temperature (25°C) for 1h. After the reaction was completed, it was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and most of the solvent was removed by spinning off. Analyze and purify, eluting with petroleum ether/ethyl acetate (V/V=15/1) to obtain 2-((tert-butoxycarbonyl)amino)-5-phenyl-4-pentynoic acid (2.6g), Then add 10% Pd/C (1.16g) dissolved in a mixed solution of EtOH (15mL) and THF (15mL), react under H2 at room temperature (25) for 2h, after removing the solvent, add 20% (V /V) In TFA/CH2Cl2 (30mL), the reaction mixture was stirred at room temperature (25°C) for 1h, the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and most of the solvent was removed by spin-off and reconstituted with n-hexane. Crystallized to obtain 2-amino-5-phenylvaleric acid (2.57 g) with a yield of 89%.
		5.C C. C. 2-(R)-Amino-5-phenyl-pentanoic acid A mixture of 440 mg (1.19 mmol) of 5B and 120 mg of palladium chloride in 20 mL of ethanol and 10 mL of THF was hydrogenated at 45 psi. for about 16 h. The mixture was filtered through diatomaceous earth and concentrated, and the residue was triturated with ether to give 240 mg of 5C as a white solid.
		5.C C. C. 2-(R)-Amino-5-phenyl-pentanoic acid A mixture of 440 mg (1.19 mmol) of 5 B and 120 mg of palladium chloride in 20 mL of ethanol and 10 mL of THF was hydrogenated at 45 psi. for about 16 h. The mixture was filtered through diatomaceous earth and concentrated, and the residue was triturated with ether to give 240 mg of 5 C as a white solid.

4
N-[(1,1-dimethylethoxy)carbonyl]amino-(2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate [ No CAS ]
[ 4392-24-9 ]
[ 36061-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hexamethyldisilazane; trifluoroacetic acid In tetrahydrofuran; ethanol; hexane; dichloromethane; sodium hydrogencarbonate	73.A (2R)-2-amino-5-phenyl-pentanoic acid Step A (2R)-2-amino-5-phenyl-pentanoic acid To a stirred solution of N-[(1,1-dimethylethoxy)carbonyl]amino-(2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate, (1.0 g, 2.8 mmol) and cinnamyl bromide (2.78 g, 14 mmol) in dry THF (70 mL) at -78° C., was added dropwise sodium hexamethyldisilazide (5.6 mL; 1.0M solution in hexane). The reaction mixture was stirred for 30 minutes, then poured into ethyl acetate (150 mL) and washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The crude product was first washed with warm hexane and then with an ether:hexane (1:1) mixture. The solid material was the desired product. A solution of this intermediate (1.0 g, 2.1 mmol) in CH2 Cl2 (2 mL) and TFA (2 mL) was stirred at room temperature for 1 h. The solvents were removed under reduced pressure and the residue was dissolved in saturated aqueous sodium bicarbonate solution and extracted with CHCl3. The organic layer was washed with brine, dried over potassium carbonate, filtered and evaporated to give the amine as a foam which was used without purification. Approximately 0.6 g (1.62 mmol) of this material was dissolved in 40 mL of (2:1) EtOH:THF and hydrogenated under 40 psi using PdCl2 /C for 24 h. The catalyst was filtered off through celite pad and the solvent was evaporated to give the title compound as a colorless solid. 1 H NMR (400MHz, CD3 OD) δ7.2 (m, 5H), 3.77 (t, 1H), 2.6 (t, 2H), 1.9 (m, 4H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5578593, 1996, A

5
[ 36061-08-2 ]
[ 103290-07-9 ]
[ 159635-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In 1,4-dioxane; water	199.C C. C. 2(R)-(2-Tert-Butoxycarbonylamino-2-Methyl-Propionylamino)-5-Phenyl-Pentanoic Acid To a solution of the compound of Example 199, Step B (130 mg, 0.67 mmol) in dioxane:water (4:1, 5 mL) was added triethylamine (0.28 mL, 2 mmol) and Example 1, Step D (201 mg, 0.67 mmol). The mixture was stirred at 45° C. for 16 h, diluted with EtOAc (20 mL) and water (10 mL) and acidified to pH 2 with HOAc. The organic phase was collected, washed with saturated NaHCO3 and brine solutions, dried over MgSO4 and concentrated to quantitatively give crude Example 199, Step C (298 mg): +APcl MS (M+1)+379, (M-tBu+1)+323, (M-Boc+1)+279; 1H NMR=400 MHz (CDCl3) δ: 7.21 (m, 2H), 7.14 (m, 3H), 4.51 (m, 1H), 1.38 (s, 9H).

Reference： [1]Current Patent Assignee: PFIZER INC - US6251902, 2001, B1

6
C₂HF₃O₂*C₁₂H₁₇NO₂ [ No CAS ]
[ 36061-08-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride In water at 80℃; for 6h; optical yield given as %ee;

Reference： [1]Location in patent: body text Murai, Yuta; Hatanaka, Yasumaru; Kanaoka, Yuichi; Hashimoto, Makoto [Heterocycles, 2009, vol. 79, # C, p. 359 - 364]

7
[ 130047-14-2 ]
[ 36061-08-2 ]
[ 1021707-70-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (2R)-2-amino-5-phenylpentanoic acid With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Reflux; Stage #2: 4-[(chlorosulfonyl)methyl]benzoic acid methyl ester With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1.75h;	2.1.g 1.3 g (6.72 mmol) of H-d-Ppg-OH (Peptech, Burlington, Mass.) were suspended in 90 ml of dry DCM, and 2 ml (15.7 mmol) of TMS-Cl and 2.6 ml (15 mmol) of DIEA were added. The mixture was refluxed for 1 h, the clear solution was cooled to 0° C., and 2 g (8 mmol) of 3-MeOOC-Bzls-Cl and 2.6 ml of DIEA were added. The mixture was stirred at 0° C. for 15 min and at RT for 1.5 h. The solvent was removed in vacuo, and the residue was dissolved in 700 ml of half-saturated NaHCO3 solution. The mixture was extracted 2× with a little ethyl acetate, and then the aqueous phase was acidified with HCl (pH about 2-3). The mixture is extracted 3× with 150 ml of ethyl acetate, and the combined ethyl acetate phase is washed 2× with 5% KHSO4 solution and 1× with saturated NaCl solution. The organic phase is dried with Na2SO4, and the solvent is removed in vacuo.Yield: 2.4 g of oil (HPLC: 33.53 min, Start with 20% B)

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US2010/22781, 2010, A1 Location in patent: Page/Page column 20

8
[ 36061-08-2 ]
[ 1939-99-7 ]
[ 1322746-50-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃;	[0091] Bzls-DPpg-OH; [0092] To a mixture of DPpg (3 g, 15 mmol) in aqueous 1M NaOH (15 ml, 15 mmol), dioxane (100 ml) and water (30 ml) was added in parallel a solution of Bzls-chloride (4.4 g, 23 mmol) in dioxane (10 ml) and aqueous 1M NaOH (25 ml, 25 mmol) at 0 °C over a period of 60 min. The pH was maintained between 8-9 by addition of aqueous 1M NaOH. The mixture was stirred at room temperature overnight. Additional Bzls-chloride (6 g, 31 mmol) and aqueous 1M NaOH (31 ml, 31 mmol) was added at 0 °C in portions and the pH maintained between 8-9 by addition of aqueous 1M NaOH. Stirring was continued until no more starting material was detected by TLC. The solvent was evaporated in vacuo and the residue portioned between ethyl acetate and aqueous 5 % KHS04. The organic layer was washed with aqueous 5 % KHSO4 and brine, dried (Na2S04), and evaporated in vacuo to afford the title compound.Yield: 4 g (75 %, white solid).Anal. HPLC: 69.3 % B; MS calc: 347.1, found 346.3 (M-H)~ [0093] (3-MeOOC)Bzls-DPpg-OH

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2011/94496, 2011, A2 Location in patent: Page/Page column 26

9
[ 36061-08-2 ]
C₄₄H₅₀N₆O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / 1,4-dioxane; water / 0 - 20 °C / pH 8 - 9 2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2011/94496, 2011, A2

10
[ 36061-08-2 ]
Bzls-DPpg-hAla(4-Pip)-4-Amba x 2TFA [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydroxide / 1,4-dioxane; water / 0 - 20 °C / pH 8 - 9 2.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C 3.1: hydrogen / palladium 10% on activated carbon / water; acetic acid / 20 °C / Inert atmosphere 3.2: 1 h / 20 °C 3.3: Chromatography

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2011/94496, 2011, A2

11
[ 36061-08-2 ]
methyl 3-[(chlorosulfonyl)methyl]benzoate [ No CAS ]
[ 1021707-70-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: (2R)-2-amino-5-phenylpentanoic acid With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Reflux; Stage #2: methyl 3-[(chlorosulfonyl)methyl]benzoate With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	[0093] (3-MeOOC)Bzls-DPpg-OH; [0094] To a suspension of DPpg (1.3 g, 6.7 mmol) in dry DCM (90 ml) was added TMS-C1 (2 ml, 15.7 mmol) and DIEA (2.6 ml, 15 mmol) at room temperature and the mixture was refluxed for 1 h with stirring. The clear solution was cooled to 0°C and (3-MeOOC)Bzls- chloride (2 g, 8 mmol) and DIEA (2.6 ml) was added. The mixture was stirred at 0°C for 15 min and at room temperature for 1.5 h. The solvent was evaporated in vacuo and the residue dissolved in half- saturated aqueous NaHC03 (700 ml) followed by extraction with ethyl acetate. The aqueous layer was acidified with aqueous HC1 (pH about 2-3) and extracted with ethyl acetate. The organic layer was washed with aqueous 5% KHS04 and brine, dried (Na2S04), and evaporated in vacuo to afford the title compound.Yield: 2.4 g (88 %, amorphous yellow solid).Anal. HPLC: 69.2 min % B; MS calc: 405.1, found 404.3 (M-H)~

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2011/94496, 2011, A2 Location in patent: Page/Page column 27

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H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 36061-08-2 ]

Quality Control of [ 36061-08-2 ]

Related Doc. of [ 36061-08-2 ]

Product Details of [ 36061-08-2 ]

Calculated chemistry of [ 36061-08-2 ]

Physicochemical Properties

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Water Solubility

Medicinal Chemistry

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[ 36061-08-2 ] Synthesis Path-Downstream 1~11

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