6049-54-3|3-Amino-3-(4-hydroxyphenyl)propanoic Acid| Ambeed

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Quality Control of [ 6049-54-3 ] Purity: 95% SDS Specification

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Product Details of [ 6049-54-3 ]

CAS No. :	6049-54-3
Formula :	C₉H₁₁NO₃
M.W :	181.19
SMILES Code :	NC(CC(O)=O)C1=CC=C(O)C=C1
MDL No. :	MFCD00181810

Safety of [ 6049-54-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 6049-54-3 ]

* 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.

Downstream synthetic route of [ 6049-54-3 ]

[ 6049-54-3 ] Synthesis Path-Downstream 1~30

1
[ 7400-08-0 ]
[ 6049-54-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1912,vol. 389,p. 36,111.

2
methyl p-hydroxycinnamate [ No CAS ]
[ 6049-54-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1912,vol. 389,p. 36,111.

3
[ 5678-45-5 ]
[ 6049-54-3 ]

References: [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2234,2236; engl. Ausg. S. 2293, 2294.

4
[ 141-82-2 ]
[ 123-08-0 ]
[ 6049-54-3 ]
[ 17449-03-5 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2242,2245; engl. Ausg. S. 2279, 2281.

5
[ 141-82-2 ]
[ 123-08-0 ]
[ 6049-54-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With ammonium acetate; In butan-1-ol;Reflux;	General procedure: A mixture of appropriate aldehyde 2.40 g (1-15), 2.44 g ofmalonic acid and 3.54 g of ammonium acetate (1:1.1:2.3), in 200mLof the 1-butanol was refluxed for 1.5-2 h until the evolution of CO2ceased. The precipitate formed was filtered and washed withboiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and100mL of water. Precipitates were dried at 80-100 C for 8-10 h.Purity of product was checked by TLC, and yield obtained about65-80% in each reaction.
65%		To a 2 liter three-mouth flask in of hydroxy benzaldehyde (100 g, 0 . 82 µM), ammonia acetate (126 g, 1 . 64 µM) and volume than 97.5% of ethanol (1.2 L). 40 C when stirring 30 minutes; then adding malonic acid (170 g, 1 . 64 µM), heating reflux for 60 hours. After cooling to room temperature, filtering and separating the white solid, for the volume ratio of 1:1 of ethanol and water mixed solution (100 ml) washing, vacuum drying to obtain a white solid, compound 1 (88.8 g, 0 . 53 µM, 65%).

References: [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 252 - 268.
[2]Patent: CN107382761,2017,A .Location in patent: Paragraph 0009; 0010; 0011.
[3]Journal fur praktische Chemie (Leipzig 1954),1965,vol. 30,p. 18 - 38.
[4]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2755 - 2758.

7
[ 6049-54-3 ]
[ 2937-50-0 ]
3-allyloxycarbonylamino-3-(4-allyloxycarbonyloxy-phenyl)-propionic acid [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 7401 - 7404.

8
[ 6049-54-3 ]
[ 103-80-0 ]
[ 329013-03-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2755 - 2758.

9
[ 6049-54-3 ]
[ 73025-68-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2755 - 2758.
[2]Patent: CN107382761,2017,A .

10
[ 6049-54-3 ]
[ 329013-12-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2755 - 2758.
[2]Patent: CN107382761,2017,A .

11
[ 6049-54-3 ]
βTyr-Pro-Trp-PheNH2 [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2755 - 2758.

12
[ 696-59-3 ]
[ 6049-54-3 ]
[ 865233-86-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; acetic acid; at 100℃; for 1h;	3-(4-Hydroxyphenyl)-3-(1H-pyrrol-1-yl)propanoic acid (55.1). At 100 C., 2,5-dimethoxytetrahydrofuran (8.5 mmol) was added to a mixture of <strong>[6049-54-3]3-amino-3-(4-hydroxyphenyl)propanoic acid</strong> (7.7 mmol) and sodium acetate (46 mmol) in acetic acid (34 mL). After stirring for 1 h, acetic acid was removed under reduced pressure. The residue was extracted with ethyl acetate (300 mL). The organic layer was washed with brine and dried over anhydrous Na2SO4 and concentrated. The residue was purified via column chromatography (10% methanol in dichloromethane) to compound 55.1. LC-MS (neg.) m/e: 230.2 (M-H).

References: [1]Patent: US2006/4012,2006,A1 .Location in patent: Page/Page column 66.

13
potassium bicarbonate [ No CAS ]
[ 24424-99-5 ]
[ 6049-54-3 ]
methyl N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxy-phenyl)propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In methanol; dichloromethane; water;	(i) Thionyl chloride (4.3 ml) was added to methanol (50 ml) cooled in an ice-salt bath. 3-Amino-3-(4-hydroxyphenyl)propionic acid (9.7 g) was added and the mixture allowed to reach ambient temperature and then refluxed for 2 hours. The solvent was removed by evaporation in vacuo to give a gummy solid (12.8 g) which was used without further purification. A solution of di-t-butyldicarbonate (5.8 g) in dichloromethane (50 ml) was added to a stirred mixture of the gummy solid (5.75 g) and potassium hydrogen carbonate (6.2 g) in water (20 ml). The mixture was stirred at ambient temperature for 4 hours. The organic layer was separated and washed with water (10 ml), 1M hydrochloric acid solution (10 ml), saturated sodium hydrogen carbonate solution (10 ml), water (10 ml) and dried (MgSO4). The solvent was evaporated to give methyl 3-(t-butyloxycarbonylamino)-3-(4-hydroxyphenyl)propionate as a solid; m.p. 119-120 C.; NMR(d6 DMSO): 1.34(s,9H), 2.54-2.78(m,2H), 3.53(s,3H), 4.7-4.9(q,1H), 6.67(d,2H), 7.08(d,2H), 7.28(brd,1H), 9.24(brs,1H).
	With thionyl chloride; In methanol; dichloromethane; water;	(i) Thionyl chloride (4.3 ml) was added to methanol (50 ml) cooled in an ice-salt bath. 3-Amino-3-(4-hydroxyphenyl)propionic acid (9.7 g) was added and the mixture allowed to reach ambient temperature and then refluxed for 2 hours. The solvent was removed by evaporation in vacuo to give a gummy solid (12.8 g) which was used without further purification. A solution of di-t-butyldicarbonate (5.8 g) in dichloromethane (50 ml) was added to a stirred mixture of the gummy solid (5.75 g) and potassium hydrogen carbonate (6.2 g) in water (20 ml). The mixture was stirred at ambient temperature for 4 hours. The organic layer was separated and washed with water (10 ml), 1M hydrochloric acid solution (10 ml), saturated sodium hydrogen carbonate solution (10 ml), water (10 ml) and dried (MgSO4). The solvent was evaporated to give methyl 3-(t-butyloxycarbonylamino)-3-(4-hydroxyphenyl)propionate as a solid; m.p. 119-120 C.; NMR(d6 DMSO): 1.34(s,9H), 2.54-2.78(m,2H), 3.53(s,3H), 4.7-4.9(q,1H), 6.67(d,2H), 7.08(d,2H), 7.28(brd, 1H), 9.24(brs,1H).
	With thionyl chloride; In methanol; dichloromethane; water;	(i) Thionyl chloride (4.3 ml) was added to methanol (50 ml) cooled in an ice-salt bath. 3-Amino-3-(4-hydroxyphenyl)propionic acid (9.7 g) was added and the mixture allowed to reach ambient temperature and then refluxed for 2 hours. The solvent was removed by evaporation in vacuo to give a gummy solid (12.8 g) which was used without further purification. A solution of di-t-butyldicarbonate (5.8 g) in dichloromethane (50 ml) was added to a stirred mixture of the gummy solid (5.75 g) and potassium hydrogen carbonate (6.2 g) in water (20 ml). The mixture was stirred at ambient temperature for 4 hours. The organic layer was separated and washed with water (10 ml), 1M hydrochloric acid solution (10 ml), saturated sodium hydrogen carbonate solution (10 ml), water (10 ml) and dried (MgSO4). The solvent was evaporated to give methyl 3-(t-butyloxycarbonylamino)-3-(4-hydroxyphenyl)propionate as a solid; m.p. 119-120 C.; NMR(d6 DMSO): 1.34(s,9H), 2.54-2.78(m,2H), 3.53(s,3H), 4.7-4.9(q,1H), 6.67(d,2H), 7.08(d,2H), 7.28(brd,1H), 9.24(brs,1H).

References: [1]Patent: US5556977,1996,A .
[2]Patent: US5652242,1997,A .
[3]Patent: US5753659,1998,A .

14
[ 6049-54-3 ]
tert-butyl 4-{3-[(3R)-3-({3-methoxy-1-[4-(2-[(4-methylphenyl)sulfonyl]oxy}ethoxy)phenyl]-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2013/23795,2013,A1 .

15
[ 6049-54-3 ]
[ 1423135-25-4 ]

References: [1]Patent: WO2013/23795,2013,A1 .

16
[ 6049-54-3 ]
[ 1423134-34-2 ]

References: [1]Patent: WO2013/23795,2013,A1 .

17
[ 6049-54-3 ]
[ 1423134-50-2 ]

References: [1]Patent: WO2013/23795,2013,A1 .

18
[ 6049-54-3 ]
[ 1423134-66-0 ]

References: [1]Patent: WO2013/23795,2013,A1 .

19
[ 67-56-1 ]
[ 6049-54-3 ]
[ 166954-93-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With thionyl chloride; at 0 - 20℃; for 20h;	5.298 g (29.24 mmol) commercial <strong>[6049-54-3]3-amino-3-(4-hydroxyphenyl)propionic acid</strong> were suspended in 136 ml methanol, the mixture cooled to 0 C and 3.20 ml (43.86 mmol) thionyl chloride were slowly added. The mixture was stirred at room temperature for 20 hours and concentrated. The residue was treated with saturated sodium hydrogen carbonate solution and extracted with dichloromethane and dichloromethane/2-propanol 8:2. The organic part was concentrated to give 5.09 g (80 %) <strong>[6049-54-3]3-amino-3-(4-hydroxyphenyl)propionic acid</strong> methyl ester. UPLC (ACN-HCOOH): Rt. = 0.45 min MS (ES*): m/e = 179.07 (M + H+-NH3) MS (ES -): m/e = 240.30 (M + HCOO-)

References: [1]Patent: WO2013/23795,2013,A1 .Location in patent: Page/Page column 112;113.

20
[ 540-88-5 ]
[ 6049-54-3 ]
[ 166023-23-0 ]
[ 166023-24-1 ]

Yield	Reaction Conditions	Operation in experiment
236.18 mg; 232.7 mg	With perchloric acid; at 15 - 20℃; for 1.5h;	1.00 g (5.52 mmol) commercial 3-amino-3-(4-hydroxy-phenyl)-propionic acid were suspended in 20 ml tert-butyl acetate and the mixture cooled to 15 C. 0.90 ml (11.10 mmol) perchloric acid were slowly added and the mixture stirred at 20 C for 1.5 hours. The solution was extracted with saturated sodium hydrogen carbonate solution. The aqueous layer was brought to pH=8 with sodium carbonate and extracted with ethyl acetate. The organic parts were combined, dried over sodium sulfate and concentrated to yield 1.0 g (60 %) racemic <strong>[6049-54-3]3-amino-3-(4-hydroxyphenyl)propionic acid</strong> tert-butyl ester. This was separated into the enantiomers by HPLC: System: 2x Labomatic Pumpe HD-3000, Labomatic AS-3000, Knauer DAD 2600, Labomatic Labcol Vario 4000 Plus Column: Chiralpak AD-H 5pm 250x50 mm Solvent: Hexane / IPA 90:10+ 0.1% Diethylamine Flow: 100 mL/min Temperature: RT UPLC (ACN-NH3): Rt. = 0.81 min MS (ES m/e = 239.18 (M + H+) MS (ES-): m/e = 236.18 (M - H), 282.18 (M + HCOO-) Optical rotation (P2000 Polarimeter, CHCl3): [α]D = -13.6 +/- 0.11 Literature: [α]D = -8.5 ( Tetrahedron: Asymmetry 18 (2007) 1554-1566, 3.6.72 Compound (S)-46)

References: [1]Patent: WO2013/23795,2013,A1 .Location in patent: Page/Page column 173; 174.

21
[ 6049-54-3 ]
[ 1423134-13-7 ]

References: [1]Patent: WO2013/23795,2013,A1 .

22
[ 6049-54-3 ]
[ 1423134-67-1 ]

References: [1]Patent: WO2013/23795,2013,A1 .

23
[ 6049-54-3 ]
[ 1423134-68-2 ]

References: [1]Patent: WO2013/23795,2013,A1 .

24
[ 908094-01-9 ]
[ 6049-54-3 ]
[ 84131-91-9 ]
C₂₀H₂₉NO₅ [ No CAS ]
[ 1448510-86-8 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 11193 - 11204.

25
[ 6049-54-3 ]
(S)-3-Boc-amino-3-(4-hydroxyphenyl)-propanoic acid [ No CAS ]

References: [1]Patent: CN107382761,2017,A .

26
[ 6049-54-3 ]
[ 152786-27-1 ]

References: [1]Patent: CN107382761,2017,A .

27
[ 24424-99-5 ]
[ 6049-54-3 ]
C₁₄H₁₉NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; In water; acetone; at 20℃; for 2h;Cooling with ice;	To the 3 liter three-mouth flask in adding compound 1 (170 g, 0 . 94 µM), triethylamine (285 g, 2.8 µM) and the volume ratio of 1:1 of acetone, water mixed solution (1.7 L). In ice by adding two carbon acid tert-butyl ester (305 g, 1.4 µM), stirring at room temperature for 2 hours. The reaction liquid petroleum ether (500 ml x 3) extraction, the aqueous phase is 1 M hydrochloric acid to pH equal to 2, then ethyl acetate (500 ml x 3) extraction. The combined organic phase, respectively for 1 M hydrochloric acid (200 ml), saturated saline solution (500 ml) washing, drying with anhydrous sodium sulfate. The filtrate turns on lathe does, to obtain white solid, compound 2 (259 g, 0 . 92 µM, 98%).

References: [1]Patent: CN107382761,2017,A .Location in patent: Paragraph 0009.

28
[ 85-44-9 ]
[ 6049-54-3 ]
3-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	at 250℃;	General procedure: Compounds in three series (16-60) were synthesized by fusedreaction. Equimolar (1:1) amount of appropriate 3-amino-3-arylpropionic acids and phthalic anhydride (series B), trimelliticanhydride (series C) and 4-methylphthalic anhydride (series D)were grinded to form homogenised mixture. The mixture wastaken in 50 mL reaction flask and placed in oil bath at 250 C, untilthe mixture fused. The reaction flask was kept at room temperaturefor 30 min and product was obtained. The product was recrystallizedin methanol and washed with acetone and chloroform. Purityof productwas checked by TLC, and yield obtained about 85-90% ineach reaction.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 252 - 268.

29
[ 6049-54-3 ]
[ 552-30-7 ]
2-(2-carboxy-1-(4-hydroxyphenyl)ethyl)-1,3-dioxoisoindoline-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	at 250℃;	General procedure: Compounds in three series (16-60) were synthesized by fusedreaction. Equimolar (1:1) amount of appropriate 3-amino-3-arylpropionic acids and phthalic anhydride (series B), trimelliticanhydride (series C) and 4-methylphthalic anhydride (series D)were grinded to form homogenised mixture. The mixture wastaken in 50 mL reaction flask and placed in oil bath at 250 C, untilthe mixture fused. The reaction flask was kept at room temperaturefor 30 min and product was obtained. The product was recrystallizedin methanol and washed with acetone and chloroform. Purityof productwas checked by TLC, and yield obtained about 85-90% ineach reaction.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 252 - 268.

30
[ 19438-61-0 ]
[ 6049-54-3 ]
3-(4-hydroxyphenyl)-3-(5-methyl-1,3-dioxoisoindolin-2-yl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	at 250℃;	General procedure: Compounds in three series (16-60) were synthesized by fusedreaction. Equimolar (1:1) amount of appropriate 3-amino-3-arylpropionic acids and phthalic anhydride (series B), trimelliticanhydride (series C) and 4-methylphthalic anhydride (series D)were grinded to form homogenised mixture. The mixture wastaken in 50 mL reaction flask and placed in oil bath at 250 C, untilthe mixture fused. The reaction flask was kept at room temperaturefor 30 min and product was obtained. The product was recrystallizedin methanol and washed with acetone and chloroform. Purityof productwas checked by TLC, and yield obtained about 85-90% ineach reaction.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 252 - 268.

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Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

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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

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CAS No.: 6049-54-3

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CAS No.: 6049-54-3

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[ 6049-54-3 ] Synthesis Path-Downstream 1~30

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