[ CAS No. 147266-79-3 ] {[proInfo.proName]}

Name: 147266-79-3|(2S,4S)-1-(tert-Butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid|97%
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SKU: A142503
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Quality Control of [ 147266-79-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 147266-79-3 ]

SDS Specification

Alternatived Products of [ 147266-79-3 ]

Product Details of [ 147266-79-3 ]

CAS No. :	147266-79-3	MDL No. :	MFCD06656447
Formula :	C₁₆H₂₁NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IQFZJNCETIGXIO-STQMWFEESA-N
M.W :	307.34	Pubchem ID :	2756009
Synonyms :

Calculated chemistry of [ 147266-79-3 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	84.38
TPSA :	76.07 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) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.7
Log Po/w (XLOGP3) :	2.6
Log Po/w (WLOGP) :	2.15
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	1.11
Consensus Log Po/w :	2.02

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.19
Solubility :	0.199 mg/ml ; 0.000647 mol/l
Class :	Soluble
Log S (Ali) :	-3.85
Solubility :	0.0437 mg/ml ; 0.000142 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.38
Solubility :	1.28 mg/ml ; 0.00416 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.5

Safety of [ 147266-79-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 147266-79-3 ]

* 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 [ 147266-79-3 ]
Downstream synthetic route of [ 147266-79-3 ]

[ 147266-79-3 ] Synthesis Path-Upstream 1~3

1
[ 93967-75-0 ]
[ 147266-79-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium hydroxide In tetrahydrofuran	(Step 2) Synthesis of (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylic acid To a solution of methyl (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylate (5.31 g, 16.5 mmol) in THF (132 ml) was added 0.25N NaOH (132 ml, 33.0 mmol). The reaction mixture was stirred overnight at room temperature. The residue obtained by concentrating the reaction mixture under reduced pressure was acidified with 1N HCl, followed by extraction with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The crude crystals thus obtained were recrystallized from hexane-chloroform, whereby the title compound (2.96 g, 58percent) was obtained as a white crystalline powder. ¹H-NMR (DMSO-d₆) δ: 1.36 (s, 9H), 2.16 (d, J=13.2Hz, 1H), 2.56 (m, 1H), 3.46 (m, 1H), 3.71 (dt, J=12.0,5.4Hz, 1H), 4.26 (dt, J=9.5,7.1Hz, 1H), 4.99 (m, 1H), 6.85 (m, 2H), 6.94 (t, J=7.3Hz, 1H), 7.28 (t, J=7.3Hz, 1H).

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 8, p. 2725 - 2746
[2] Patent: EP1346982, 2003, A1,

2
[ 221050-87-9 ]
[ 147266-79-3 ]

Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 11, p. 1173 - 1176

3
[ 74844-91-0 ]
[ 147266-79-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 8, p. 2725 - 2746

[ 147266-79-3 ] Synthesis Path-Downstream 1~33

1
[ 23357-46-2 ]
[ 147266-79-3 ]
(2S,4S)-4-Phenoxy-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

2
[ 40004-08-8 ]
[ 147266-79-3 ]
[ 886447-83-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2725 - 2746

3
[ 93967-75-0 ]
[ 147266-79-3 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium hydroxide; In tetrahydrofuran;	(Step 2) Synthesis of (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylic acid To a solution of methyl (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylate (5.31 g, 16.5 mmol) in THF (132 ml) was added 0.25N NaOH (132 ml, 33.0 mmol). The reaction mixture was stirred overnight at room temperature. The residue obtained by concentrating the reaction mixture under reduced pressure was acidified with 1N HCl, followed by extraction with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The crude crystals thus obtained were recrystallized from hexane-chloroform, whereby the title compound (2.96 g, 58%) was obtained as a white crystalline powder. 1H-NMR (DMSO-d6) delta: 1.36 (s, 9H), 2.16 (d, J=13.2Hz, 1H), 2.56 (m, 1H), 3.46 (m, 1H), 3.71 (dt, J=12.0,5.4Hz, 1H), 4.26 (dt, J=9.5,7.1Hz, 1H), 4.99 (m, 1H), 6.85 (m, 2H), 6.94 (t, J=7.3Hz, 1H), 7.28 (t, J=7.3Hz, 1H).

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2725 - 2746
[2]Patent: EP1346982,2003,A1

4
[ 74844-91-0 ]
[ 147266-79-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2725 - 2746

5
[ 108-95-2 ]
methylenedigallic acid [ No CAS ]
[ 147266-79-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2725 - 2746

6
[ 147266-79-3 ]
[ 886447-39-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2725 - 2746

7
[ 147266-79-3 ]
[4-((2S,4S)-1-{2-[3-Methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-4-phenoxy-pyrrolidine-2-carbonyl)-piperazin-1-yl]-acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2725 - 2746

8
[ 147266-79-3 ]
[ 886447-49-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2725 - 2746

9
[ 147266-79-3 ]
4-phenoxy-pyrrolidine-2-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide; hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

10
[ 147266-79-3 ]
((S)-2,2-Dimethyl-1-{(2S,4S)-4-phenoxy-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

11
[ 147266-79-3 ]
H-N-Me-Ala-Tle-(4S)-4-phenoxy-Pro-(R)-tetrahydronaphth-1-yl amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

12
[ 147266-79-3 ]
H-N,N-Me₂-Ala-Tle-(4S)-4-phenoxy-Pro-(R)-tetrahydronaphth-1-yl amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

13
[ 147266-79-3 ]
((S)-1-Cyclohexyl-2-oxo-2-{(2S,4S)-4-phenoxy-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-1-yl}-ethyl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

14
[ 147266-79-3 ]
[(S)-1-((S)-2,2-Dimethyl-1-{(2S,4S)-4-phenoxy-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidine-1-carbonyl}-propylcarbamoyl)-ethyl]-methyl-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

15
[ 147266-79-3 ]
1-(2-amino-3,3-dimethyl-butyryl)-4-phenoxy-pyrrolidine-2-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide; hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

16
[ 147266-79-3 ]
[(S)-1-((S)-1-Cyclohexyl-2-oxo-2-{(2S,4S)-4-phenoxy-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-1-yl}-ethylcarbamoyl)-ethyl]-methyl-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

17
[ 147266-79-3 ]
1-(amino-cyclohexyl-acetyl)-4-phenoxy-pyrrolidine-2-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide; hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426

19
[ 147266-79-3 ]
[ 317357-19-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	In tetrahydrofuran;	To a stirred solution of <strong>[147266-79-3](2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylic acid</strong> (2.39 g, 7.76 mmol) in THF (50 ml) was added BH3.DMS (1.55 ml, 15.5 mmol) at 0 C. After 10 min. stirring at the same temperature, the mixture was allowed to room temperature and then heated at 50 C. for 2 h. After cooling to room temperature, the mixture was concentrated in vacuo and quenched by the addition of water at 0 IC. The mixture was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was chromatographed on silica gel [60 g, CHCl3/MeOH (50/1)] to give (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylmethanol (2.83 g, 100%) as a colorless oil. 1H-NMR (CDCl3) delta 1.47 (s, 9H), 1.95 (br, 1H), 2.36 (m, 1H), 3.56-3.74 (m, 3H), 3.89-4.52 (m, 3H), 4.85 (br, 1H), 6.84 (dd, J=8.8, 1.2 Hz, 2H), 6.97 (t, J=7.2 Hz, 1H), 7.29 (t, 2I, J=7.8 Hz).
100%		BH3-S(CH3)2 (5.47 mL, 57.7 mmol) was added to a soln of <strong>[147266-79-3](2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid</strong>(153, 8.87 g, 28.9 mmol) in THF (170 mL). The mixture was heated to 50 C. for 2 h, cooled to 0 C. and treated with H2O (100 mL), followed by an aqueous workup (CH2Cl2, H2O; Na2SO4). FC (hexane/EtOAc) afforded 154 (8.46 g, quant. yield).
	With borane-THF; In tetrahydrofuran; at 0 - 20℃;	To a solution of <strong>[147266-79-3](2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid</strong> 20-a (1.40 g, 4.56 mmol) in THF cooled to 0 C. was added borane tetrahydrofuran complex (18.22 ml, 18.2 mmol), the reaction was stirred at 0 C. for 15 minutes and room temperature overnight. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide intermediate 20-b as a colorless oil.

190 mg

[003 14j To a solution of (2S ,4S)- 1 -Qert-butoxycarbonyl)-4-phenoxypyrrolidine-2- carboxylic acid (200 mg, 0.65 mmol) and N-methylmorpholine (110 jiL, 0.98 mmol) inTHF (6.5 mL) at 0 C was added isobutyl chloroformate (100 jiL, 0.78 mmol). The reaction mixture was stirred for 5 minutes before sodium borohydride (98 mg, 2.6 mmol) dissolved in 5 mL of water was added portionwise. The reaction mixture was allowed to warm to rt and stir over night. The reaction was quenched with saturated ammonium chloride and extracted with EtOAc (3x). The combined organics were washed with brine,dried with sodium sulfate, filtered and concentrated to yield the title compound as a clear oil (190 mg, 0.65 mmol). (ESI) m/z 238.1 (M-tBu+H).

Reference： [1]Patent: US2003/78249,2003,A1
[2]Patent: US2012/270881,2012,A1 .Location in patent: Page/Page column 113-114
[3]Patent: US9284350,2016,B2 .Location in patent: Page/Page column 68
[4]Patent: WO2016/40417,2016,A1 .Location in patent: Paragraph 00314

20
[ 221050-87-9 ]
[ 147266-79-3 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 1173 - 1176

21
[ 95-55-6 ]
[ 147266-79-3 ]
[ 1133717-67-5 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 1173 - 1176

22
[ 95-84-1 ]
[ 147266-79-3 ]
[ 1133717-69-7 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 1173 - 1176

23
[ 1199-46-8 ]
[ 147266-79-3 ]
[ 1133717-71-1 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 1173 - 1176

24
[ 147266-79-3 ]
[ 1266099-67-5 ]

Reference： [1]Patent: US2012/270881,2012,A1

25
[ 147266-79-3 ]
C₁₁H₁₅NO₂*(x)ClH [ No CAS ]

Reference： [1]Patent: US2012/270881,2012,A1

26
[ 147266-79-3 ]
C₃₆H₄₄FN₇O₄*2ClH [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

27
[ 147266-79-3 ]
[ 317357-20-3 ]

Reference： [1]Patent: US9284350,2016,B2

28
[ 147266-79-3 ]
C₂₄H₃₁FN₂O₃ [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

29
[ 147266-79-3 ]
C₃₁H₃₄FN₅O₄ [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

30
[ 147266-79-3 ]
C₂₆H₂₆FN₅O₂*2ClH [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

31
[ 147266-79-3 ]
C₃₇H₄₅FN₆O₅ [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

32
[ 147266-79-3 ]
C₃₂H₃₇FN₆O₃*2ClH [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

33
[ 147266-79-3 ]
C₄₁H₅₂FN₇O₆ [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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. 147266-79-3 ] {[proInfo.proName]}

Quality Control of [ 147266-79-3 ]

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[ 147266-79-3 ] Synthesis Path-Upstream 1~3

[ 147266-79-3 ] Synthesis Path-Downstream 1~33

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Amino Acid Derivatives

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[ 147266-79-3 ]