[ CAS No. 621-54-5 ] {[proInfo.proName]}

Name: 621-54-5|3-(3-Hydroxyphenyl)propanoic acid|98%
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SKU: A157385
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3d Animation Molecule Structure of 621-54-5

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Quality Control of [ 621-54-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 621-54-5 ]

Product Details of [ 621-54-5 ]

CAS No. :	621-54-5	MDL No. :	MFCD00016554
Formula :	C₉H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QVWAEZJXDYOKEH-UHFFFAOYSA-N
M.W :	166.17	Pubchem ID :	91
Synonyms :		Chemical Name :	3-(3-Hydroxyphenyl)propanoic acid

Calculated chemistry of [ 621-54-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	44.82
TPSA :	57.53 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) :	-6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.06
Log Po/w (XLOGP3) :	1.36
Log Po/w (WLOGP) :	1.41
Log Po/w (MLOGP) :	1.37
Log Po/w (SILICOS-IT) :	1.4
Consensus Log Po/w :	1.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.9
Solubility :	2.1 mg/ml ; 0.0126 mol/l
Class :	Very soluble
Log S (Ali) :	-2.17
Solubility :	1.12 mg/ml ; 0.00675 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.0
Solubility :	1.67 mg/ml ; 0.0101 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.08

Safety of [ 621-54-5 ]

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

Application In Synthesis of [ 621-54-5 ]

* 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 [ 621-54-5 ]
Downstream synthetic route of [ 621-54-5 ]

[ 621-54-5 ] Synthesis Path-Upstream 1~8

1
[ 621-54-5 ]
[ 6968-35-0 ]

Reference： [1] Chemische Berichte, 1916, vol. 49, p. 2106
[2] Chemische Berichte, 1916, vol. 49, p. 2410
[3] Chemische Berichte, 1916, vol. 49, p. 2106
[4] Chemische Berichte, 1916, vol. 49, p. 2410

2
[ 621-54-5 ]
[ 6968-35-0 ]
[ 3470-49-3 ]

Reference： [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 1, p. 25 - 37

3
[ 621-54-5 ]
[ 77-78-1 ]
[ 10516-71-9 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1092,1095
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 3523,3527

4
[ 215872-63-2 ]
[ 1135-24-6 ]
[ 621-54-5 ]
[ 1135-23-5 ]
[ 331-39-5 ]
[ 102-32-9 ]
[ 306-08-1 ]
[ 1078-61-1 ]
[ 1081-71-6 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 8, p. 3356 - 3362

5
[ 215872-63-2 ]
[ 1135-24-6 ]
[ 621-54-5 ]
[ 1135-23-5 ]
[ 331-39-5 ]
[ 102-32-9 ]
[ 306-08-1 ]
[ 1078-61-1 ]
[ 23028-17-3 ]
[ 2475-56-1 ]
[ 1081-71-6 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 8, p. 3356 - 3362

6
[ 67-56-1 ]
[ 621-54-5 ]
[ 61389-68-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 60℃; for 3 h;	Intermediate 60; 3- (2-Cyclopropyl-5-hydroxy-phenyl) -propionic acid methyl ester; Step A; 3- (3 -Hydroxy-phenyl) -propionic acid (24.88 g, 149.7 <n="51"/>mmol) is dissolved in methanol (50 mL) . Thionyl chloride (5 π\\L, 68.7 mmol) is added dropwise with vigorous stirring. The mixture is stirred at 60⁰C for 3 h. Cooling and concentration yielded 3- (3 -hydroxy-phenyl) -propionic acid methyl ester 56(29.26 g, quant.) as an oil: ¹H-NMR (400 MHz, CDCl₃) δ = 7.15(dd, J = 8.4, 7.6 Hz, IH), 6.75 (d, J^" = 7.6 Hz, IH), 6.69 (m,2H), 3.68 (s, 3H), 2.90 (t, J = 7.6 Hz, 2H), 2.63 (t, J" = 7.6Hz, 2H) .
100%	at 60℃; for 3 h;	Intermediate 41; 3-(2-Cyclopropyl-5-hydroxy-phenyl)-propionic acid methyl ester; Step A; 3 -(3 -Hydroxy-phenyl) -propionic acid (24.88 g, 149.7 mmol) is dissolved in methanol (50 mL). Thionyl chloride (5 mL, 68.7 mmol) is added dropwise with vigorous stirring. The mixture is stirred at 60⁰C for 3 h. Cooling and concentration yielded 3-(3- hydroxy-phenyl)-propionic acid methyl ester 37 (29.26 g, quant.) as an oil: ¹H-NMR (400 MHz, CDCl₃) δ = 7.15 (dd, J= 8.4, 7.6 Hz, IH), 6.75 (d, J= 7.6 Hz, IH), 6.69 (m, 2H), 3.68 (s, 3H), 2.90 (t, J= 7.6 Hz, 2H), 2.63 (t, J= 7.6 Hz, 2H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5488 - 5492
[2] Patent: WO2007/56366, 2007, A2, . Location in patent: Page/Page column 49-50
[3] Patent: WO2007/56497, 2007, A1, . Location in patent: Page/Page column 34
[4] Patent: EP2952517, 2015, A1, . Location in patent: Paragraph 0217
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4204 - 4219
[6] Analytical Chemistry, 2000, vol. 72, # 10, p. 2237 - 2246
[7] Tetrahedron Asymmetry, 1998, vol. 9, # 16, p. 2915 - 2924
[8] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1939 - 1944

7
[ 621-54-5 ]
[ 61389-68-2 ]

Reference： [1] Patent: US6602878, 2003, B1,

8
[ 621-54-5 ]
[ 129150-68-1 ]

Reference： [1] Journal of Organic Chemistry, 1990, vol. 55, # 24, p. 6000 - 6017

[ 621-54-5 ] Synthesis Path-Downstream 1~108

1
[ 305-80-6 ]
[ 621-54-5 ]
3-[5-hydroxy-2-(4-sulfo-phenylazo)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Chemische Berichte,1904,vol. 37,p. 4127

2
[ 621-54-5 ]
[ 100-34-5 ]
3-(5-hydroxy-2-phenylazo-phenyl)-propionic acid [ No CAS ]
3-(5-hydroxy-2,4-bis-phenylazo-phenyl)-propionic acid [ No CAS ]

Reference： [1]Chemische Berichte,1904,vol. 37,p. 4127

3
[ 621-54-5 ]
[ 100-34-5 ]
3-(5-hydroxy-2,4-bis-phenylazo-phenyl)-propionic acid [ No CAS ]

Reference： [1]Chemische Berichte,1904,vol. 37,p. 4127

4
[ 621-54-5 ]
[ 6968-35-0 ]

Reference： [1]Chemische Berichte,1916,vol. 49,p. 2106
[2]Chemische Berichte,1916,vol. 49,p. 2106

5
[ 621-54-5 ]
[ 3470-49-3 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 5126 - 5129
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 1275 - 1281
[3]Journal of the Chemical Society,1953,p. 2403,2405

6
[ 621-54-5 ]
[ 25173-80-2 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 1107,1109

7
[ 621-54-5 ]
[ 75849-10-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1932,vol. 497,p. 47,52

8
[ 621-54-5 ]
[ 149506-38-7 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1932,vol. 497,p. 47,52

9
[ 14755-02-3 ]
[ 621-54-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 5199 - 5211
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 1186 - 1194
[3]Organic Letters,2018,vol. 20,p. 5126 - 5129
[4]Analytical Chemistry,2000,vol. 72,p. 2237 - 2246
[5]Chemische Berichte,1882,vol. 15,p. 2047
[6]Journal of the Chemical Society,1963,p. 5072 - 5094
[7]Tetrahedron,2014,vol. 70,p. 9776 - 9782

10
[ 6066-82-6 ]
[ 621-54-5 ]
[ 131450-43-6 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2007 - 2014

11
[ 4377-41-7 ]
[ 621-54-5 ]
[ 123724-17-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 240 - 245

12
[ 621-54-5 ]
[ 100-39-0 ]
[ 57668-34-5 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

13
[ 863-03-6 ]
[ 621-54-5 ]
[ 31129-95-0 ]
[ 6500-64-7 ]
[ 31129-94-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 888 - 893

14
[ 863-03-6 ]
[ 621-54-5 ]
[ 31129-95-0 ]
[ 31129-94-9 ]
[ 111397-00-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 888 - 893

15
[ 863-03-6 ]
[ 621-54-5 ]
[ 31129-95-0 ]
[ 31129-94-9 ]
(4R)-5-(3-hydroxyphenyl)-γ-valerolactone [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 888 - 893

16
[ 863-03-6 ]
[ 621-54-5 ]
[ 31129-95-0 ]
[ 31129-94-9 ]
[ 191666-22-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 888 - 893

17
[ 863-03-6 ]
[ 621-54-5 ]
[ 31129-95-0 ]
[ 31129-94-9 ]
2'',3''-dihydroxyphenoxyl (3',4'-dihydroxyphenyl)propionate [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 888 - 893

18
[ 863-03-6 ]
[ 621-54-5 ]
[ 31129-95-0 ]
[ 31129-94-9 ]
(2S)-1-(3'-hydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 888 - 893

19
[ 863-03-6 ]
[ 621-54-5 ]
[ 31129-95-0 ]
[ 31129-94-9 ]
[ 490-46-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 888 - 893

20
[ 67-56-1 ]
[ 621-54-5 ]
[ 61389-68-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; at 60℃; for 3h;	Intermediate 60; 3- (2-Cyclopropyl-5-hydroxy-phenyl) -propionic acid methyl ester; Step A; 3- (3 -Hydroxy-phenyl) -propionic acid (24.88 g, 149.7 <n="51"/>mmol) is dissolved in methanol (50 mL) . Thionyl chloride (5 ?L, 68.7 mmol) is added dropwise with vigorous stirring. The mixture is stirred at 600C for 3 h. Cooling and concentration yielded 3- (3 -hydroxy-phenyl) -propionic acid methyl ester 56(29.26 g, quant.) as an oil: 1H-NMR (400 MHz, CDCl3) delta = 7.15(dd, J = 8.4, 7.6 Hz, IH), 6.75 (d, J" = 7.6 Hz, IH), 6.69 (m,2H), 3.68 (s, 3H), 2.90 (t, J = 7.6 Hz, 2H), 2.63 (t, J" = 7.6Hz, 2H) .
100%	With thionyl chloride; at 60℃; for 3h;	Intermediate 41; 3-(2-Cyclopropyl-5-hydroxy-phenyl)-propionic acid methyl ester; Step A; 3 -(3 -Hydroxy-phenyl) -propionic acid (24.88 g, 149.7 mmol) is dissolved in methanol (50 mL). Thionyl chloride (5 mL, 68.7 mmol) is added dropwise with vigorous stirring. The mixture is stirred at 600C for 3 h. Cooling and concentration yielded 3-(3- hydroxy-phenyl)-propionic acid methyl ester 37 (29.26 g, quant.) as an oil: 1H-NMR (400 MHz, CDCl3) delta = 7.15 (dd, J= 8.4, 7.6 Hz, IH), 6.75 (d, J= 7.6 Hz, IH), 6.69 (m, 2H), 3.68 (s, 3H), 2.90 (t, J= 7.6 Hz, 2H), 2.63 (t, J= 7.6 Hz, 2H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492
[2]Patent: WO2007/56366,2007,A2 .Location in patent: Page/Page column 49-50
[3]Patent: WO2007/56497,2007,A1 .Location in patent: Page/Page column 34
[4]Patent: EP2952517,2015,A1 .Location in patent: Paragraph 0217
[5]Journal of Medicinal Chemistry,2015,vol. 58,p. 4204 - 4219
[6]Analytical Chemistry,2000,vol. 72,p. 2237 - 2246
[7]Tetrahedron Asymmetry,1998,vol. 9,p. 2915 - 2924
[8]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1939 - 1944

21
[ 14755-02-3 ]
[ 7732-18-5 ]
sodium amalgam [ No CAS ]
[ 621-54-5 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 2047

22
[ 621-54-5 ]
[ 100-52-7 ]
[ 100-46-9 ]
[ 389635-00-1 ]
[ 627535-88-0 ]

Reference： [1]Organic letters,2001,vol. 3,p. 4079 - 4082

23
[ 621-54-5 ]
[ 120-20-7 ]
[ 78-84-2 ]
[ 389635-00-1 ]
(R)-2-((R)-2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-[3-(3-hydroxy-phenyl)-propionyl]-amino}-3-methyl-butyrylamino)-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 4079 - 4082

24
[ 104-53-0 ]
[ 621-54-5 ]
[ 75-31-0 ]
[ 389635-00-1 ]
[ 627535-87-9 ]

Reference： [1]Organic letters,2001,vol. 3,p. 4079 - 4082

25
[ 64-17-5 ]
[ 621-54-5 ]
[ 34708-60-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfuric acid; for 2h;Heating / reflux;	A solution of <strong>[621-54-5]3-(3-hydroxyphenyl)propionic acid</strong> (Lancaster, 66.4 g, 0.4 mol) in ethanol (700 mL) was treated with concentrated sulfuric acid (6 mL), heated to reflux for 2 h, and allowed to cool to RT. The mixture was cooled in ice, neutralized with 10% aqueous sodium carbonate and concentrated in vacuo to about 50 mL. Water (200 nmL) was added and the mixture was extracted three-times with ethyl acetate. The combined ethyl acetate extract was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to yield the title compound as an oil (70 g, 90%).
	toluene-4-sulfonic acid; for 4h;Heating / reflux;	A solution of 3-Hydroxyphenylpropanoic acid (25 g, 150.60 mmol) and p- Toluenesulfonic acid monohydrate (3.80 g, 20 mmol) in abs ethanol (250 ml) was refluxed for 4 hours or until all the starting material is consumed. The reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound.1H NMR (270 MHz, CDCl3): 1.2 (t, 3H); 2.6 (t, 2H); 2.8 (t, 2H); 4.2 (q, 2H); 6.7-6.8 (m, 3H); 7.2 (m, IH).
	With sulfuric acid; at 20℃; for 24h;Heating / reflux;	To a solution of 3- (3-hydroxyphenyl) propanoic acid (135 g) in EtOH (670 mL) was added concentrated H2SO4 (34.7 mL) at ambient temperature and the mixture was refluxed for 24 hours.After cooled to ambient temperature, the mixture was evaporated in vacuo. Water (400 mL) was added to the mixture and the mixture was extracted with EtOAc (600 mL) . The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford ethyl 3- (3- hydroxyphenyl) propanoate (163 g) as a slightly yellow oil.1H-NMR(CDCl3)0: 1.24 (3H, t, J=7. IHz) ,2.61 (2H, t , J=7.5Hz) ,2.90 (2H,t, J=7.5Hz) ,4.13(2H,q, J=7.1Hz) ,4.32-4.58 (IH, brs) , 6.65-6.72 (2H,m) ,6.76(lH,d, J=7.7Hz) ,7.15-7.18 (lH,m) .

30 g

With sulfuric acid; In ethanol; for 2h;Reflux;

(a) 3-(3-Hydroxy-phenyl)-propionic acid ethyl ester To a solution of commercially available 3-(3-hydroxy-phenyl)-propionic acid (25 g, 150.4 mmol) in ethanol (250 mL) was added concentrated sulfuric acid (3.0 mL). The solution was heated to reflux overnight. The solvent was removed in vacuo, and the resulting oil was diluted ethyl acetate and placed in a separatory funnel. The organic portion was extracted 2* with 5% NaHCO3 and once with brine. The solution was dried (MgSO4), filtered and concentrated to a dark tan oil (30 g). This material was carried on to the next step without further purification.

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1495 - 1503
[2]Organic Process Research and Development,2012,vol. 16,p. 1544 - 1551
[3]Patent: US2004/14723,2004,A1 .Location in patent: Page/Page column 6-7
[4]Patent: WO2007/56771,2007,A2 .Location in patent: Page/Page column 40-41
[5]Patent: WO2008/72784,2008,A1 .Location in patent: Page/Page column 110
[6]Patent: US9227914,2016,B2 .Location in patent: Page/Page column 11; 24

26
[ 621-54-5 ]
[ 1758-46-9 ]
C₁₇H₁₉NO₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4689 - 4693

27
[ 621-54-5 ]
[ 494865-03-1 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1495 - 1503

28
[ 621-54-5 ]
3-{3-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1495 - 1503

29
[ 621-54-5 ]
3-[3-(hydroxyimino-methyl)-phenyl]-propionic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492

30
[ 621-54-5 ]
C₁₁H₁₂ClNO₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492

31
[ 621-54-5 ]
3-(3-trifluoromethanesulfonyloxy-phenyl)-propionic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492

32
[ 621-54-5 ]
3-(3-{4-[2-(2,4-dichloro-phenoxy)-ethyl-carbamoyl]-5-phenyl-isoxazol-3-yl}-phenyl)-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492

33
[ 621-54-5 ]
[ 927187-49-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492

34
[ 621-54-5 ]
[ 62876-44-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492

35
[ 621-54-5 ]
[ 193151-11-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5488 - 5492

36
[ 621-54-5 ]
11-isopropyl-20-nitro-10,13-dioxo-12-phenethyl-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 7859 - 7870

37
[ 621-54-5 ]
12-isopropyl-4-nitro-10,13-dioxo-11-phenethyl-2-oxa-9,12-diaza-tricyclo[14.2.2.2^3,6]docosa-1⁽¹⁹⁾,3,5,16⁽²⁰⁾,17,21-hexaene-8-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 4079 - 4082

38
[ 621-54-5 ]
12-[2-(3,4-dimethoxy-phenyl)-ethyl]-11-isopropyl-4-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.2^3,6]docosa-1⁽¹⁹⁾,3,5,16⁽²⁰⁾,17,21-hexaene-8-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 4079 - 4082

39
[ 621-54-5 ]
[ 274928-12-0 ]

Reference： [1]Analytical Chemistry,2000,vol. 72,p. 2237 - 2246

40
[ 621-54-5 ]
[ 274928-11-9 ]

Reference： [1]Analytical Chemistry,2000,vol. 72,p. 2237 - 2246

41
[ 621-54-5 ]
[ 222556-16-3 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 2109 - 2112

42
[ 621-54-5 ]
[ 222556-25-4 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 2109 - 2112

43
[ 621-54-5 ]
(S)-5-(3-Benzyloxy-benzyl)-3-((S)-1-hydroxymethyl-2-phenyl-ethyl)-imidazolidine-2,4-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 2109 - 2112

44
[ 621-54-5 ]
[ 222556-20-9 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 2109 - 2112

45
[ 621-54-5 ]
[ 222556-26-5 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 2109 - 2112

46
[ 621-54-5 ]
[ 222556-14-1 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 2109 - 2112

47
[ 621-54-5 ]
[ 222556-19-6 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 2109 - 2112

48
[ 621-54-5 ]
3-(3-acetoxypropyl)phenol [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 2915 - 2924

49
[ 621-54-5 ]
3-(3-Hydroxy-phenyl)-N-[2-(4-hydroxy-phenyl)-ethyl]-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1186 - 1194

50
[ 621-54-5 ]
3-(3-Hydroxy-phenyl)-N-[2-(3-hydroxy-phenyl)-ethyl]-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1186 - 1194

51
[ 621-54-5 ]
[ 188662-10-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1186 - 1194

52
[ 621-54-5 ]
3-(3-Hydroxy-phenyl)-N-{3-[3-(3-hydroxy-phenyl)-propionylamino]-propyl}-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1186 - 1194

53
[ 621-54-5 ]
(E)-5-hydroxy-2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1275 - 1281

54
[ 621-54-5 ]
(S)-3-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-6-[3-(3-hydroxy-phenyl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2007 - 2014

55
[ 621-54-5 ]
(S)-3-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-6-[3-(3-sulfooxy-phenyl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2007 - 2014

56
[ 621-54-5 ]
[ 136480-31-4 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

57
[ 621-54-5 ]
[ 143215-95-6 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

58
[ 621-54-5 ]
[ 136645-24-4 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

59
[ 621-54-5 ]
[ 136451-64-4 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

60
[ 621-54-5 ]
[ 143215-94-5 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

61
[ 621-54-5 ]
[ 136451-63-3 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

62
[ 621-54-5 ]
[ 136451-89-3 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

63
[ 621-54-5 ]
[ 136645-18-6 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

64
[ 621-54-5 ]
[ 136451-58-6 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

65
[ 621-54-5 ]
[ 143215-60-5 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3483 - 3497

66
[ 621-54-5 ]
[ 129150-68-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

67
[ 621-54-5 ]
3-{4-[3-(2-Amino-ethyl)-phenoxy]-phenyl}-propionic acid methyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

68
[ 621-54-5 ]
[ 132513-29-2 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

69
[ 621-54-5 ]
[ 120363-32-8 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

70
[ 621-54-5 ]
3-{4-[3-(2-tert-Butoxycarbonylamino-ethyl)-phenoxy]-phenyl}-propionic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

71
[ 621-54-5 ]
[ 129150-69-2 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

72
[ 621-54-5 ]
[ 129150-71-6 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

73
[ 621-54-5 ]
3-(4-{3-[2-(2-tert-Butoxycarbonylamino-acetylamino)-ethyl]-phenoxy}-phenyl)-propionic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

74
[ 621-54-5 ]
[ 120363-40-8 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017
[2]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017
[3]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

75
[ 621-54-5 ]
[ 129150-81-8 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

76
[ 621-54-5 ]
[ 129150-75-0 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

77
[ 621-54-5 ]
(S)-2-(3-{4-[3-(2-tert-Butoxycarbonylamino-ethyl)-phenoxy]-phenyl}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

78
[ 621-54-5 ]
3-[4-(3-{2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

79
[ 621-54-5 ]
[ 129150-76-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

80
[ 621-54-5 ]
[ 120363-28-2 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

81
[ 621-54-5 ]
[ 129150-82-9 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

82
[ 621-54-5 ]
[ 120363-34-0 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

83
[ 621-54-5 ]
[ 120363-43-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

84
[ 621-54-5 ]
(S)-2-(3-{4-[3-(2-tert-Butoxycarbonylamino-ethyl)-phenoxy]-phenyl}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid pentafluorophenyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

85
[ 621-54-5 ]
[ 120363-35-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 6000 - 6017

86
[ 621-54-5 ]
[ 123723-94-4 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 240 - 245

87
[ 621-54-5 ]
[ 123724-02-7 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 240 - 245

88
[ 621-54-5 ]
[ 119514-95-3 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 240 - 245

89
[ 621-54-5 ]
[ 66192-02-7 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 3523,3527

90
[ 621-54-5 ]
[ 5411-61-0 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 3523,3527

91
[ 621-54-5 ]
[ 121484-76-2 ]

Reference： [1]Journal of the Chemical Society,1959,p. 1613
[2]Tetrahedron,2014,vol. 70,p. 9776 - 9782

92
[ 99-61-6 ]
[ 621-54-5 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 2047

93
[ 100-83-4 ]
[ 621-54-5 ]

Reference： [1]Chemische Berichte,1882,vol. 15,p. 2047

94
[ 621-54-5 ]
[ 1971-83-1 ]

Reference： [1]Journal of the Chemical Society,1963,p. 5072 - 5094

95
[ 621-54-5 ]
[ 33753-45-6 ]

Reference： [1]Journal of the Chemical Society,1963,p. 5072 - 5094

96
[ 621-54-5 ]
4-Aminomethyl-cyclohexanecarboxylic acid 3-(2-carboxy-ethyl)-phenyl ester [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 247 - 255

97
[ 621-54-5 ]
4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid 3-(2-benzyloxycarbonyl-ethyl)-phenyl ester [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 247 - 255

98
[ 621-54-5 ]
[ 28945-92-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1970,vol. 736,p. 110 - 125

99
[ 67-66-3 ]
[ 621-54-5 ]
[ 1100596-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; water; at 70℃; for 12h;	Scheme IX illustrates the preparation of aldehydes 21. For example, a compound of formula 20 wherein R3, R4 and R5 are hydrogen, i.e., <strong>[621-54-5]3-(3-hydroxyphenyl)propionic acid</strong>, (3.0 g, 0.018 mol, Aldrich Chemical Comp, Cat 1279), NaOH (6 g, 0.15 mol), water (40 mL), and chloroform (40 ml) were combined and heated at 70 C. for 12 h in a 100 ml round bottom flask. The solution is acidified to pH 4, extracted with EtOAc (2×30 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to give 3-(4-formyl-3-hydroxy phenyl)propionic acid which was used without further purification.

Reference： [1]Patent: US6867200,2005,B1 .Location in patent: Page/Page column 24

100
[ 183306-87-8 ]
[ 621-54-5 ]
[ 183307-29-1 ]

Reference： [1]Patent: US6350746,2002,B1 .Location in patent: Page column 37

101
[ 621-54-5 ]
[ 100-39-0 ]
[ 149506-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide; dichloromethane; water;	Benzyl 3-(3-benzyloxyphenyl)propionate 16.6 g of <strong>[621-54-5]3-(3-hydroxyphenyl)propionic acid</strong>, 27.7 g of potassium carbonate and 36 ml of benzyl bromide in 150 ml of dimethylformamide are stirred at ambient temperature for 17 hours. Then another 10 g of potassium carbonate and 10 ml of benzyl bromide are added and the mixture is stirred for 7 hours at ambient temperature, then for one day at 50 C. and later for one day at 100 C. After cooling, the mixture is added to 1 liter of water, extracted with ethyl acetate and the organic phase is dried over sodium sulphate and evaporated down. After chromatography over a silica gel column with cyclohexane/methylene chloride (5:1), 17.7 g (51% of theory) are obtained. Rf value: 0.76 (silica gel; methylene chloride)
	With potassium carbonate; In N,N-dimethyl-formamide; at 65℃; for 16h;	A mixture of 3-(3-hydroxyphenyl)propanoic acid (Fluorochem, 12.46 g, 75 mmol), potassium carbonate (31.1 g, 225 mmol), and benzyl bromide (18.7 ml, 158 mmol) in DMF (120 ml) was stirred at 65 0C for 16 h. The mixture was cooled to room temperature, diluted with ether (200 ml) and water (400 ml) and the aq re-extracted with ether (100 ml). The combined organics were washed with water (3 x 100 ml), dried (magnesium sulphate) and evaporated to give an almost colourless oil (26.5 g) which was used without purification. 1H NMR (CDCI3) delta 2.68 (2H, t), 2.94 (2H, t), 5.01 (2H, s), 5.1 1 (2H, s), 6.78-6.82 (3H, m), 7.17-7.43 (11 H, m).
	With potassium carbonate; In acetone;Heating / reflux;	A mixture of 3- (3-hydroxyphenylpropionic acid) (15 g, 0.09 mole), and K2C03 (48.9 g, 0. 35 mol), dissolved in acetone (200 ml) was treated dropwise with benzyl bromide (22.5 ml, 0.19 mole). The reaction was stirred overnight at reflux, and concentrated after cooling. The residue was diluted with water and then acidified-with conc. HCI. After extracting with EtOAc, the organic layer was washed with brine, dried over Na2S04, and concentrated to yield 34.49 g of the product as a liquid. IH NMR (CDC13) : 5 : 2.68 (2H, t), 2.95 (2H, t), 5.02 (2H, s), 5.11 (2H, s), 6.74-6. 83 (3H, m), 7.17-7. 21 (1H, m), 7.29-7. 44 (1OH, m). CI+ Mass Spec: m/e 346 (M+).

	With potassium carbonate; In acetonitrile;Heating / reflux;	A solution of <strong>[621-54-5]3-(3-hydroxyphenyl)propionic acid</strong> (6.70 g, 40.3 mmol), benzyl bromide (12 ml, 101 mmol), and potassium carbonate (16.7 g, 121 mmol) in acetonitrile (100 mL) was refluxed overnight. After cooling to room temperature, diethyl ether (100 mL) was added to the reaction mixture. The solid in the solution was removed by filtration. The filtrate was concentrated to a residue. The residue was dissolved in THF (40 mL) and methanol (40 mL). Sodium hydroxide solution (1.0 N, 60 mL, 60 mmol) was added. The resulting solution was stirred at room temperature for 3 hours. The organic solvent was evaporated, and the aqueous phase was extracted with diethyl ether twice. Addition of hydrochloric acid (2.0 N) formed a precipitate which was collected as a white solid. MH-=255.0
3.68 g	With potassium carbonate; In N,N-dimethyl-formamide; at 10 - 35℃;	A) benzyl 3-(3-(benzyloxy)phenyl)propanoate (0964) A mixture of 311 3-(3-hydroxyphenyl)propanoic acid (2 g), 312 benzyl bromide (2.86 ml), 28 potassium carbonate (2.16 g) and 21 DMF (30 ml) was stirred at room temperature overnight. To the reaction mixture was added 29 water and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the 313 title compound (3.68 g). 1H NMR (300 MHz, DMSO-d6) delta 2.64-2.76 (2H, m), 2.79-2.91 (2H, m), 5.05 (2H, s), 5.08 (2H, s), 6.75-6.86 (2H, m), 6.89 (1H, d, J = 1.6 Hz), 7.12-7.22 (1H, m), 7.26-7.48 (10H, m).
	With potassium carbonate; In acetonitrile; at 15 - 80℃; for 10h;	[0336] To a solution of compound 3-(3-hydroxyphenyl)propanoic acid (1.00 g, 6.02 mmol) in acetonitrile (10 mL) was added potassium carbonate (2.1 g, 15 mmol) and benzyl bromide (1.57 mL, 13.2 mmol) at 15C and the mixture was stirred at 80C for 10 hours. The reaction was poured into water (50 mL) and the solution was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide 1-89-1 as a colorless oil (2.3 g, crude) which was used directly without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3158 - 3160
[2]Patent: US5541343,1996,A
[3]Patent: WO2009/80730,2009,A1 .Location in patent: Page/Page column 26
[4]Patent: WO2003/95441,2003,A1 .Location in patent: Page/Page column 132-133
[5]Patent: US2007/232630,2007,A1 .Location in patent: Page/Page column 17
[6]Patent: EP3225618,2017,A1 .Location in patent: Paragraph 0964
[7]Patent: WO2019/75259,2019,A1 .Location in patent: Paragraph 0336

102
[ 621-54-5 ]
[ 34708-60-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfuric acid; In ethanol; water;	a Ethyl 3-hydroxybenzenepropionate A solution of <strong>[621-54-5]3-(3-hydroxyphenyl)propionic acid</strong> (Lancaster, 66.4 g, 0.4 mol) in ethanol (700 mL) was treated with concentrated sulfuric acid (6 mL), heated to reflux for 2 h, and allowed to cool to RT. The mixture was cooled in ice, neutralized with 10% aqueous sodium carbonate and concentrated in vacuo to about 50 mL. Water (~200 mL) was added and the mixture was extracted three-times with ethyl acetate. The combined ethyl acetate extract was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to yield the title compound as an oil (70 g, 90%).
	With thionyl chloride; In ethanol; ethyl acetate; toluene;	1) To an ice-cooled solution of <strong>[621-54-5]3-(3-hydroxyphenyl)propionic acid</strong> (20.0 g, 120 mmol) in ethanol was dropwise added thionyl chloride (8.8 ml, 120 mmol). The mixture was stirred at room temperature over night, concentrated in vacuo and submitted to flash chromatography (10% ethyl acetate in toluene eluent) to give 23.3 g of 3-(3-hydroxy-phenyl)propionic acid ethyl ester. 1H NMR (CDCL3): delta 1.25 (3H, t), 2.60 (2H, t), 2.88 (2H, t), 4.13 (2H, q), 6.65-6.75 (3H, m), 7.05-7.15 (1H, m).

Reference： [1]Patent: US2003/18203,2003,A1
[2]Patent: US2003/139473,2003,A1

103
[ 621-54-5 ]
[ 222978-10-1 ]
[ 1972-28-7 ]
[ 254451-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; In tetrahydrofuran;	Step G: Preparation of 1-(4-cyano-3-fluorobenzyl)-5-[((3-(3-hydroxyphenyl)propionyl)oxy)methyl]imidazole To a solution of the alcohol from Step F (79.7 mg, 0.345 mmol) and triphenylphosphine (90.0 mg, 0.345 mmol) in 0.5 mL of THF was added a solution of diethylazodicarboxylate (0.054 mL, 0.345 mmol) and <strong>[621-54-5]3-(3-hydroxyphenyl)propionic acid</strong> (57 mg, 0.34 mmol) in 0.5 mL of THF. After 10 minutes, HPLC analysis indicated 60% conversion. Additional triphenylphosphine (45 mg, 0.17 mmol) and diethylazodicarboxylate (0.027 mL, 0.17 mmol) were added, and the reaction was stirred for 10 more minutes. The solution was concentrated in vacuo, then purified by silica gel chromatography (3% MeOH/CH2Cl2) to provide the desired product as a white foam.

Reference： [1]Patent: US6358985,2002,B1

104
[ 621-54-5 ]
[ 61389-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In methanol;	Stage A: Methyl 3-Hydroxy-benzenepropanoate 1 g of 3-hydroxy-benzenepropanoic acid is mixed in 20 ml of methanol and 8 drops of sulphuric acid, the reaction medium is taken to reflux for 2 hours then evaporated under reduced pressure and purified by chromatography eluding with an AcOEt/Cyclohexane mixture 50/50. 1.07 g of expected product is obtained. IR (CHCl3): 3595 cm-1 and associated (OH); 1732 cm-1 (C=O of the methyl ester, Me: 1439 cm-1); 1614, 1599, 1591, 1491 cm-1 Aromatic.

Reference： [1]Patent: US6602878,2003,B1

105
[ 621-54-5 ]
[ 6482-24-2 ]
[ 1000896-90-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 60℃;	To <strong>[621-54-5]3-(3-hydroxyphenyl)propionic acid</strong> (8.31 g, 50 mmol, 1 eq) in N,N-dimethylformamide (150 ml) was added potassium carbonate (17.28 g, 125 mmol, 3 eq) followed by 2-bromoethyl methyl ether (10.34 ml, 110 mmol, 2.20 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated to dryness. The residue was extracted into ethyl acetate, washed with water and brine, dried with magnesium sulphate, filtered and evaporated to yield a yellow oil 11.38 g. The reaction mixture was purified by column chromatography using a gradient of 0-30% ethyl acetate in hexanes. To this intermediate (9.82 g, 43.76 mmol, 1 eq) was added N,N-dimethylformamide (50 ml) followed by potassium carbonate (9.1 g, 65.64 mmol, 2.5 eq) and 2-bromoethyl methyl ether (4.94 ml, 52.5 mmol, 1.2 eq). The reaction mixture was heated at 60 C. for 18 h. The reaction mixture was diluted with N,N-dimethylformamide (50 ml) and a further 4.55 g of potassium carbonate was added followed by 2-bromoethyl methyl ether (2.45 ml). The reaction mixture was heated overnight at 60 C. for a further 20 h. After cooling to room temperature, the inorganics were filtered and the solvent was evaporated under reduced pressure. The residue was extracted into ethyl acetate and the organic layers was washed with water, saturated sodium hydrogen carbonate and brine. After drying (magnesium sulphate) and filtration, the organic layers were evaporated under reduced pressure to yield a yellow oil. The crude product was purified by column chromatography, eluting with a gradient of 0-50% ethyl acetate in hexanes. The desired product was obtained as a clear yellow oil (8.755 g, 71%).

Reference： [1]Patent: US2008/153812,2008,A1 .Location in patent: Page/Page column 95

106
[ 1031421-47-2 ]
[ 621-54-5 ]
C₃₀H₄₁N₇O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2536 - 2539

107
[ 1073545-51-3 ]
[ 621-54-5 ]
[ 1073543-82-4 ]

Yield	Reaction Conditions	Operation in experiment
28%		3-(3-(((6-Cyclopropyl-2'-fluoro-5'-(methyloxy)-l,l'-biphenyl-3- yl)methyl)oxy)phenyl)propanoic acid (13).; To a solution of 3-(3- hydroxyphenyl)-propionic acid (0.031 g, 0.186 mmol) (commercially available from Alfa, CAS No. 621-54-5) in THF (1 mL) was added tetrabutylphosphonium hydroxide (40 wt % solution in water) (0.27 g, 0.39 mmol). The mixture was then cooled in an ice bath to 0 0C. After 10 minutes, 13.5 (0.055 g, 0.191 mmol) was added at 0 0C. Upon complete addition, the reaction was allowed to warm to room temperature. After 44 hours, the solvent was removed under vacuum. The residue was diluted with water and acidified with 2M HCl to pH 2. The mixture was extracted with EtOAc. The layers were separated and the solvent was removed under vacuum to yield an oil that was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 65% EtOAc in hexanes) to yield a colorless film 13 (0.023 g, 28% yield.) 1H NMR (400 MHz, CDCl3) delta ppm 7.39 (IH, dd, J= 8.0, 1.8 Hz), 7.31 (IH, d, J= 2.0 Hz), 7.23 (IH, t, J= 8.0 Hz), 7.10 (IH, m), 6.99 (IH, d, J= 7.8 Hz), 6.90 (5H, m), 5.04 (2H, s), 3.82 (3H, s), 2.95 (2H, t, J= 7.8 Hz), 2.72 (2H, m), 1.85 (IH, m), 0.87 (2H, m), 0.68 (2H, m).

Reference： [1]Patent: WO2008/130514,2008,A1 .Location in patent: Page/Page column 87-88

108
[ 621-54-5 ]
[ 52615-97-1 ]
C₂₄H₂₉NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 4.0h;	[0456] To a solution of 0.250 g (1.50 mmol) of 3-(3-hydroxyphenyl)propanoic acid in DMF (7 mL) was added 0.500 g (1.58 mmol) of 4-benzyl l-(tert-butyl) L-aspartate hydrochloride followed by 0.65 g (1.7 mmol) of HATU and 0.90 mL (5.2 mmol) of DIEA. The mixture was stirred at room temperature for 4 hours then diluted with water and extracted with EtOAc. The combined organic phase was washed with IN HC1 followed by saturated aqueous sodium bicarbonate and brine. The mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography and the eluent was concentrated under reduced pressure to provide 3-18-3 (0.587 g, 91%) as a clear oil.

Reference： [1]Patent: WO2019/75259,2019,A1 .Location in patent: Paragraph 0456

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 621-54-5 ] {[proInfo.proName]}

Quality Control of [ 621-54-5 ]

Related Doc. of [ 621-54-5 ]

Product Details of [ 621-54-5 ]

Calculated chemistry of [ 621-54-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 621-54-5 ]

Application In Synthesis of [ 621-54-5 ]

[ 621-54-5 ] Synthesis Path-Upstream 1~8

[ 621-54-5 ] Synthesis Path-Downstream 1~108

Related Functional Groups of [ 621-54-5 ]

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 621-54-5 ]