7292-74-2|2-Amino-2-(3-fluorophenyl)acetic acid| Ambeed

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Quality Control of [ 7292-74-2 ] Purity: 98% SDS Specification

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Product Details of [ 7292-74-2 ]

CAS No. :	7292-74-2
Formula :	C₈H₈FNO₂
M.W :	169.15
SMILES Code :	O=C(O)C(N)C1=CC=CC(F)=C1
MDL No. :	MFCD00049325
InChI Key :	LVYBCZIDQKJNFP-UHFFFAOYSA-N
Pubchem ID :	265434

Safety of [ 7292-74-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 7292-74-2 ]

* 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 [ 7292-74-2 ]

[ 7292-74-2 ] Synthesis Path-Downstream 1~35

1
[ 24424-99-5 ]
[ 7292-74-2 ]
[ 142121-94-6 ]

Yield	Reaction Conditions	Operation in experiment
69%		To a suspension of <strong>[7292-74-2]2-amino-2-(3-fluorophenyl)acetic acid</strong> (1.00 g, 5.91 mmol) in THF (30 ml) and water (30 ml), 2N sodium hydroxide (29.6 ml, 59.1 mmol) and di-tert-butyl dicarbonate (2.58 g, 1 1.8 mmol) were added and the reaction was stirred at RT for 15h. THF was evaporated, the aqueous phase was cooled and acidified with 37% HCl until pH 1. The desired compound was extracted with EtOAc and the organic phase was washed with brine, dried over Na2SO4 and evaporated to obtain 2-(tert-butoxycarbonylamino)-2-(3- fluorophenyl)acetic acid (1.10 g; 69% yield).
69%	With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 15h;	To a suspension of <strong>[7292-74-2]2-amino-2-(3-fluorophenyl)acetic acid</strong> (1.00 g, 5.91 mmol) in THF (30 ml) and water (30 ml), were added 2N sodium hydroxide (29.6 ml, 59.1 mmol) and di-tert-butyl dicarbonate (2.58 g, 11.8 mmol), and the reaction was stirred at RT for 15 hours. THF was evaporated, and the aqueous phase was cooled and acidified with 37% HCl until pH 1. The desired compound was extracted with EtOAc, and the organic phase was washed with brine, dried over Na2SO4 and evaporated to obtain 2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetic acid (1.10 g; 69% yield).

References: [1]Patent: WO2012/69275,2012,A1 .Location in patent: Page/Page column 64-65.
[2]Patent: US2012/134934,2012,A1 .Location in patent: Page/Page column 30.
[3]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.

2
(3-Fluoro-phenyl)-[(E)-hydroxyimino]-acetic acid [ No CAS ]
[ 7292-74-2 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.

3
[ 271583-22-3 ]
[ 7292-74-2 ]

References: [1]Synthetic Communications,2000,vol. 30,p. 1095 - 1102.

Yield	Reaction Conditions	Operation in experiment
		Substitution in the procedure of Example 3 for the N-tert.-butoxycarbonyl derivative of D-α-aminophenylacetic acid (also called D-α-tert.-butoxycarboxamidophenylacetic acid) of an equimolar weight of the N-tert.-butoxycarbonyl derivative of ... D-α-amino-m-methylphenylacetic acid, D-α-amino-p-chlorophenylacetic acid, D-α-amino-m-chlorophenylacetic acid, D-α-amino-p-fluorophenylacetic acid, D-α-amino-m-fluorophenylacetic acid, D-α-amino-p-aminophenylacetic acid, D-α-amino-p-dimethylaminophenylacetic acid, D-α-amino-m,p-dimethoxyphenylacetic acid, ...
		The hydantoin was hydrolyzed at reflux using 1 N NaOH giving 2-amino-2-(3-fluorophenyl)acetic acid which was esterified via Procedure H in methanol to give the title compound.

5
[ 271583-58-5 ]
[ 7292-74-2 ]

References: [1]Synthetic Communications,2000,vol. 30,p. 1095 - 1102.

6
[ 271583-37-0 ]
[ 7292-74-2 ]

References: [1]Synthetic Communications,2000,vol. 30,p. 1095 - 1102.

7
[ 456-48-4 ]
[ 7292-74-2 ]

References: [1]Synthetic Communications,2000,vol. 30,p. 1095 - 1102.

8
[ 501-00-8 ]
[ 7292-74-2 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.

9
[ 7292-74-2 ]
(R)-1-[2-tert-Butoxycarbonylamino-2-(3-fluoro-phenyl)-acetyl]-pyrrolidine-2-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.

10
[ 7292-74-2 ]
C₂₀H₁₇Cl₃FNO₆ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.

11
[ 7292-74-2 ]
C₃₂H₄₁FN₆O₇ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.

12
[ 7292-74-2 ]
[2-{(S)-2-[(S)-1-(Benzyloxycarbonylamino-imino-methyl)-2-oxo-piperidin-3-ylcarbamoyl]-pyrrolidin-1-yl}-1-(3-fluoro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.

13
[ 7292-74-2 ]
Boc-D-Phg(F)-Pro-Arg-H*HOAc [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.

14
[ 7292-74-2 ]
rac-2-amino-2-(3-fluorophenyl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃;Heating;	D,L-3-fluorophenylglycine (10 g, 59.2 mmol) was added to a suspension of NaBH4 (5.37 g, 142 mmol) in THF (200 mL). The suspension was cooled to 0 C., and an iodine solution (15 g, 59.2 mmol) in THF was added drop wise. The resulting solution was heated while stirring overnight. This solution was cooled to room temperature, quenched with a 20% KOH solution (150 mL) and extracted with DCM (3×). The organics were combined, dried over MgSO4 and the solvent was removed using a rotary evaporator. The product was purified by flash chromatography (0-10% MeOH/EtOAc) to yield 2-amino-2-(3-fluorophenyl)ethanol (I-8) as a white residue.
	With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃; for 20h;Reflux;	Step 1: Preparation of 2-amino- -(3-fluoro-phenyl)-ethanol Amino-(3-fluoro-phenyl)-acetic acid (1.8 g, 10 mmol), NaBH4 (0.95 g, 2.5 mmol) and THF (30 mL) were added dropwise to a solution of iodine (2.54 g, 10 mmol) in anhydrous THF (7 mL) through a pressure-equalizing addition funnel at 0 C. After the ceasing of the hydrogen gas, the reaction mixture was heated to reflux for 20 hours and then cooled to room temperature. The reaction was quenched with methanol, and then dissolved in 20% aqueous KOH. The reaction mixture was stirred overnight to give 1.4 g of crude 2-amino-2-(3-fluoro-phenyl)- ethanol which was directly used in the next step.
	With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃;Heating;	In step 2-1, D,L-3-fluorophenylglycine (10 g, 59.2 mmol) was added to a suspension Of NaBH4 (5.37 g, 142 mmol) in THF (200 mL). The suspension was cooled to 0 0C, and an iodine (15 g, 59.2 mmol) solution in THF was added drop- wise. The resulting solution was heated while stirring over-night. This solution was cooled to room temperature, quenched with a 20 % KOH solution (150 mL), and extracted with dichloro methane (3x). The organics were combined, dried over MgSO4 and the solvent removed using a rotary evaporator. The product was purified with flash chromatography (0 -10 % methanol/ethyl acetate) to yield 2-amino-2-(3-fluorophenyl)ethanol (2-1) as a white residue.

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 562 - 567.
[2]Patent: US2012/65184,2012,A1 .Location in patent: Page/Page column 37-38.
[3]Patent: WO2014/106606,2014,A1 .Location in patent: Page/Page column 64.
[4]Patent: WO2009/140128,2009,A2 .Location in patent: Page/Page column 102.

15
[ 7292-74-2 ]
[ 1196551-87-7 ]

References: [1]Patent: US2012/65184,2012,A1 .
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 562 - 567.
[3]Patent: WO2009/140128,2009,A2 .

16
[ 7292-74-2 ]
[ 1196551-88-8 ]

References: [1]Patent: US2012/65184,2012,A1 .
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 562 - 567.
[3]Patent: WO2009/140128,2009,A2 .

17
[ 7292-74-2 ]
[ 1196551-89-9 ]

References: [1]Patent: US2012/65184,2012,A1 .
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 562 - 567.
[3]Patent: WO2009/140128,2009,A2 .

18
[ 7292-74-2 ]
[ 1196551-90-2 ]

References: [1]Patent: US2012/65184,2012,A1 .
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 562 - 567.
[3]Patent: WO2009/140128,2009,A2 .

19
[ 7292-74-2 ]
[ 1365212-63-0 ]

References: [1]Patent: US2012/65184,2012,A1 .

20
[ 7292-74-2 ]
[ 1365212-76-5 ]

References: [1]Patent: US2012/65184,2012,A1 .

21
[ 7292-74-2 ]
[ 1365212-77-6 ]
(S)-6-(2-(3-fluorophenyl)-2,5-dihydro-1H-pyrrol-1-yl)imidazo[1,2-b]pyridazine-3-carboxamide [ No CAS ]

References: [1]Patent: US2012/65184,2012,A1 .

22
[ 7292-74-2 ]
[ 1379513-71-9 ]

References: [1]Patent: WO2012/69275,2012,A1 .
[2]Patent: US2012/134934,2012,A1 .

23
[ 7292-74-2 ]
[ 1379513-70-8 ]

References: [1]Patent: WO2012/69275,2012,A1 .
[2]Patent: US2012/134934,2012,A1 .

24
[ 7292-74-2 ]
[ 1617545-71-7 ]

References: [1]Patent: WO2014/106606,2014,A1 .

25
[ 7292-74-2 ]
[ 1196547-19-9 ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 562 - 567.

26
[ 91-02-1 ]
[ 7292-74-2 ]
3-(3-fluorophenyl)-1-phenylimidazo[1,5-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With di-tert-butyl peroxide; iodine; In toluene; at 120℃; for 12h;Sealed tube;	General procedure: To a 10mL reaction tube were added L-Proline-MCM-41-Cu(OTf)2 (71mg, 0.045mmol), 2-benzoylpyridine 1 (0.3mmol), amino acid 2(0.9mmol), molecular iodine (0.045mmol), DTBP (0.75mmol), and toluene (2mL). The reaction tube was sealed and placed in an oil bath at room temperature. The reaction mixture was stirred at 120 C for 12 h. After being cooled to room temperature, the reaction mixture was diluted with 15 mL of EtOAc, and filtered. The L-Proline-MCM-41-Cu(OTf)2 complex was washed with EtOAc (25mL) and ethanol (2 5mL), and reused in the next run. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (petroleum ether: EtOAc 15:1-20:1) to provide the desired product 3.

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 3681 - 3687.
[2]Journal of Organometallic Chemistry,2019,vol. 881,p. 1 - 12.

27
[ 7292-74-2 ]
S-ethyl 3-(3-fluorophenyl)-3-((4-methoxyphenyl)amino)propanethioate [ No CAS ]

References: [1]Chemical Communications,2017,vol. 53,p. 3062 - 3065.

28
[ 7292-74-2 ]
methyl 3-(3-fluorophenyl)-3-((4-methoxyphenyl)amino)-2,2-dimethylpropanoate [ No CAS ]

References: [1]Chemical Communications,2017,vol. 53,p. 3062 - 3065.

29
[ 7292-74-2 ]
[ 104-94-9 ]
[ 64222-81-7 ]

References: [1]Chemical Communications,2017,vol. 53,p. 3062 - 3065.

30
[ 7292-74-2 ]
7-(3,5-dimethylisoxazol-4-yl)-2-(3-fluorophenyl)-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 152,p. 542 - 559.

31
[ 7292-74-2 ]
C₁₄H₉BrFNO₂ [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 152,p. 542 - 559.

32
[ 7292-74-2 ]
C₁₄H₁₀Br₂FNO₂ [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 152,p. 542 - 559.

33
[ 7292-74-2 ]
C₈H₅BrClFO [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 152,p. 542 - 559.

34
[ 7292-74-2 ]
[ 24805-50-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution ofDL-methionine (3.0 g, 20.1 mmol) in H2O (50 mL) was added 30% HBr (20 mL). The reaction mixture was stirred at 0 C for 10 min. A solution of sodium nitrite (1.7 g, 24 mmol) in H2O (50 mL) was added. The reaction mixture was stirred at 0 C for 30 min and thenwarmed to rt for 3 h. The reaction mixture was extracted withEtOAc (100 mL 3). The organic layer was washed with brine and dried over Na2SO4. The solid was filtered off, and the filtrate was concentrated under reduced pressure to give 3.6 g of intermediate 35c (83% yield).

References: [1]European Journal of Medicinal Chemistry,2018,vol. 152,p. 542 - 559.

35
[ 7292-74-2 ]
[ 1196546-34-5 ]

References: [1]Patent: WO2009/140128,2009,A2 .

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Technical Information

• Alkyl Halide Occurrence • 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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CAS No.: 7292-74-2

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CAS No.: 7292-74-2

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Product Details of [ 7292-74-2 ]

Safety of [ 7292-74-2 ]

Application In Synthesis of [ 7292-74-2 ]

[ 7292-74-2 ] Synthesis Path-Downstream 1~35

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