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Quality Control of 4-Amino-L-phenylalanine Purity: 95% SDS Specification

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Product Details of 4-Amino-L-phenylalanine

CAS No. :	943-80-6
Formula :	C₉H₁₂N₂O₂
M.W :	180.20
SMILES Code :	O=C(O)[C@@H](N)CC1=CC=C(N)C=C1
MDL No. :	MFCD00069927
InChI Key :	CMUHFUGDYMFHEI-QMMMGPOBSA-N
Pubchem ID :	151001

Safety of 4-Amino-L-phenylalanine

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

Application In Synthesis of 4-Amino-L-phenylalanine

* 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 [ 943-80-6 ]

[ 943-80-6 ] Synthesis Path-Downstream 1~41

1
[ 949-99-5 ]
[ 943-80-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With barium sulfate; hydrogen; palladium;	To a solution of Ap, a mixture of 8 g L-4-nitrophenylalanine (38 mmol) and 0.8 g barium sulfate was put in a 250 mL three-necked flask while adding the gas of hydrogen to do the hydrogenation for 4 h. The reaction mixture was filtered and concentrated to crystallization. The productions were washed with water, dried and evaporated. Finally, we added 5.9 g white powder and the yield was 87%(Fig. 1F) [19].
85%	With rosenmund catalyst; hydrogen; In water; at 20℃; for 3h;	A mixed solution of concentrated HNO3 (60%) and concentrated H2SO4 (1.4:1.1 v/v) was prepared and chilled to 10 C. Then, a portion of this solution (3.5 mL) was added dropwise under stirring to a solution of L-phenylalanine (4.139 g, 25.1 mmol) in H2SO4 (98%, 12.5 mL). The reaction mixture was stirred at 10 C for 2.5 h. The reaction solution was then adjusted to pH 5 with NH4OH. The pale yellow precipitate formed was collected by filtration, washed with a small volume of water and CH3CN, and then dried to yield 4-nitro-L-phenylalanine as a yellow powder (4.748 g, 90%). 4-Nitro-L-phenylalanine (2.006 g, 9.54 mmol) was suspended in water (35 mL) and subjected tohydrogenation at room temperature for 3 h in the presence of 0.2 g of 5% palladium-barium sulfate.The catalyst was filtered through a Celite pad, and the pale brown filtrate was concentrated. Theresidue was washed with CH3CN to afford a pale brown mass (1.460 g, 85%). No further purificationwas performed for the following step. The 4-amino-L-phenylalanine derivative (0.060 g, 0.33 mmol)was dissolved in 6N HCl (4 mL). Sodium nitrate in water (0.030 g/0.5 mL) was added at 0 C. Thereaction mixture was stirred at the same temperature for 40 min and diluted with 6N HCl (0.25 mL).Subsequently, sodium azide in water (0.033 g/0.75 mL) was added at 0 C. The reaction mixture wasstirred at same temperature for 5 min, and then warmed to room temperature for 1 h, thenconcentrated. The residue was reprecipitated from CH3CN to afford a pure colorless amorphous mass(0.0435 g, 64%). Analytical and spectroscopic data were identical to those reported in the literature [10].

References: [1]Letters in drug design and discovery,2015,vol. 12,p. 466 - 470.
[2]Molecules,2013,vol. 18,p. 8393 - 8401.
[3]Helvetica Chimica Acta,1957,vol. 40,p. 80,83.
[4]Chemistry Letters,1998,p. 704 - 706.
[5]Chemistry Letters,1998,p. 537 - 538.

2
[ 1943-83-5 ]
[ 943-80-6 ]
[ 94976-07-5 ]

References: [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 799 - 803.
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1432 - 1436.

3
[ 943-80-6 ]
[ 76912-54-4 ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 960 - 970.

4
[ 80657-95-0 ]
[ 943-80-6 ]

References: [1]Journal of the American Chemical Society,1985,vol. 107,p. 5008 - 5009.

5
[ 80657-95-0 ]
[ 943-80-6 ]
[ 150-13-0 ]
[ 97279-80-6 ]
[ 97279-79-3 ]

References: [1]Journal of the American Chemical Society,1985,vol. 107,p. 5008 - 5009.

6
[ 943-80-6 ]
[ 624-83-9 ]
[ 94976-06-4 ]

References: [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 799 - 803.
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1432 - 1436.

7
methyl p-amino-DL-phenylalaninate dihydrochloride [ No CAS ]
[ 943-80-6 ]
(R)-2-Amino-3-(4-amino-phenyl)-propionic acid methyl ester [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1225 - 1234.
[2]Journal of the Chemical Society. Perkin transactions I,1993,p. 1225 - 1234.

8
[ 943-80-6 ]
[ 14173-39-8 ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 1465 - 1471.

9
[ 943-80-6 ]
[ 57213-14-6 ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 1465 - 1471.

10
[ 943-80-6 ]
[ 154715-61-4 ]
(S)-3-(4-Amino-phenyl)-2-(4-sulfamoyl-benzoylamino)-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 559 - 564.

11
[ 943-80-6 ]
[ 176170-33-5 ]
(S)-3-(4-Amino-phenyl)-2-[2-(4-sulfamoyl-benzoylamino)-acetylamino]-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 559 - 564.

12
[ 943-80-6 ]
[ 67460-24-6 ]
(S)-3-(4-Amino-phenyl)-2-{2-[2-(4-sulfamoyl-benzoylamino)-acetylamino]-acetylamino}-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 559 - 564.

13
[ 943-80-6 ]
[ 176170-34-6 ]
(S)-3-(4-Amino-phenyl)-2-(2-{2-[2-(4-sulfamoyl-benzoylamino)-acetylamino]-acetylamino}-acetylamino)-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 559 - 564.

14
[ 943-80-6 ]
[ 23508-35-2 ]

References: [1]Tetrahedron,1996,vol. 52,p. 14501 - 14506.

15
[ 943-80-6 ]
[ 82911-69-1 ]
[ 95753-56-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2677 - 2680.

16
[ 943-80-6 ]
[ 586-96-9 ]
[ 154596-15-3 ]

References: [1]Chemistry Letters,1998,p. 704 - 706.
[2]Chemistry Letters,1998,p. 537 - 538.

18
[ 7647-01-0 ]
[ 58816-70-9 ]
[ 943-80-6 ]

References: [1]Helvetica Chimica Acta,1957,vol. 40,p. 80,83.

19
[ 7647-01-0 ]
[ 103156-14-5 ]
[ 943-80-6 ]

References: [1]Helvetica Chimica Acta,1957,vol. 40,p. 80,83.

20
[ 24424-99-5 ]
[ 943-80-6 ]
2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonylamino-phenyl)-propionic acid [ No CAS ]

References: [1]Chemistry - A European Journal,2001,vol. 7,p. 4280 - 4295.

22
[ 943-80-6 ]
[ 150304-28-2 ]
C₇₃H₁₆N₂O₂ [ No CAS ]

References: [1]Chemistry - A European Journal,2007,vol. 13,p. 2530 - 2545.

23
[ 943-80-6 ]
2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonylamino-phenyl)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester [ No CAS ]

References: [1]Chemistry - A European Journal,2001,vol. 7,p. 4280 - 4295.

24
[ 943-80-6 ]
[ 197724-51-9 ]

References: [1]Chemistry Letters,1998,p. 537 - 538.
[2]Chemistry Letters,1998,p. 704 - 706.
[3]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2677 - 2680.

25
[ 943-80-6 ]
[ 58960-71-7 ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 960 - 970.

26
[ 943-80-6 ]
[ 76912-55-5 ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 960 - 970.

27
[ 943-80-6 ]
[ 76912-56-6 ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 960 - 970.

28
[ 943-80-6 ]
N-(t-butoxycarbonyl)-3-(3',5'-dibromo-4'-chlorophenyl)alanine [ No CAS ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 960 - 970.

29
[ 943-80-6 ]
N-(t-butoxycarbonyl)-3-(3',4',5'-tribromophenyl)alanine [ No CAS ]

References: [1]Helvetica Chimica Acta,1983,vol. 66,p. 960 - 970.

30
[ 943-80-6 ]
[ 94976-08-6 ]

References: [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 799 - 803.
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1432 - 1436.

31
[ 943-80-6 ]
[ 94976-09-7 ]

References: [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 799 - 803.
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 1432 - 1436.

32
4-amino-α-benzoylamino-trans(?)-cinnamic acid-((1R)-menthyl ester) [ No CAS ]
[ 943-80-6 ]

References: [1]Helvetica Chimica Acta,1957,vol. 40,p. 80,83.

33
[ 58816-69-6 ]
[ 943-80-6 ]

References: [1]Helvetica Chimica Acta,1957,vol. 40,p. 80,83.

34
[ 943-80-6 ]
[ 53807-56-0 ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 1465 - 1471.

35
[ 943-80-6 ]
[ 57213-16-8 ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 1465 - 1471.

36
[ 943-80-6 ]
p-Chlor-m-aminophenylalanin [ No CAS ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 1465 - 1471.

37
[ 943-80-6 ]
m-Azido-phenylalanin [ No CAS ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 1465 - 1471.

38
[ 943-80-6 ]
[ 57213-15-7 ]

References: [1]Helvetica chimica acta,1975,vol. 58,p. 1465 - 1471.

39
[ 869566-16-5 ]
[ 943-80-6 ]
C₁₉H₂₁ClN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide);	To a solution of 1 (2.3 g, 12.6 mmol) in DMF (30 mL) were added 2 (4.0 g, 10.5 mmol) and N, N-diisopropylethylamine (5.2 mL, 30 mmol). The reaction was monitored by LC/MS. The resulting solution was used in the next step without further purification. LRMS (M+H+) m/z 377.1. [00219] To a solution of crude 3 in DMF (6 mL, - 2mmo) ) were added glycinamide HCI (330 mg, 3 mmol), HBTU (1.14 g, 3 mmol) and N, N-diisopropylethylamine (522 muL, 3 mmol). The reaction was stirred overnight, The resulting crude product was purified via RP- HPLC using a mixture of acetonitrile and H2O to give 4 (600 mg, 69% from 2). LRMS (M+H) m/z 433.1.

References: [1]Patent: WO2005/107762,2005,A2 .Location in patent: Page/Page column 134-135.

40
CH₂ Cl₂:MeOH [ No CAS ]
[ 943-80-6 ]
[ 14608-95-8 ]
[ 501-53-1 ]
5-(N-benzyloxycarbonyl-((p-benzyloxycarbonylamino)phenyl-alanyl)-valylamino)-1,3,4-thiadiazole-2-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 16 Synthesis of 5-(N-benzyloxycarbonyl-((p-benzyloxycarbonylamino)phenyl-alanyl)-valylamino)-1,3,4-thiadiazole-2-thione N-Benzyloxycarbonyl-(p- benzyloxycarbonylamino)-phenylalanine compound was prepared using Schotten-Baumann conditions (Bodanszky, "Principles of Peptide Synthesis") as described in Examples 14 and 15 starting with (L)-<strong>[943-80-6]4-amino-phenylalanine</strong> (Bachem Bioscience, King of Prussia, Pa.) and using two equivalents of Cbz-Cl. The procedure described in Example 11, using N-benzyloxycarbonyl-(p-benzyloxycarbonylamino)phenylalanine in place of N-benzyloxycarbonyl-(O-benzyl) tyrosine, was used to complete the synthesis. An analytical sample was prepared by preparative TLC using CH2 Cl2:MeOH (95:5), Rf =0.22. Melting point 195.2-203.4 C. 1 H-NMR (d6 -DMSO, int. std.) 14.1 (br s, 1/2H, NH thiadiazole) 12.6 (br s, 1/2H, NH amide thiadiazole) 9.7(d, 1H, amide) 8.2 (d 1H, amide) 7.3 (m 15H, aromatic+amide) 5.2 (s, 2H, CH2 CBZ on para-amino group) 4.9 (s, 2H, CH2 -CBZ on alpha nitrogen) 4.3 (m, 2H, 2*chiral) 2.0 (app s, 1H, CH valine) 0.8 (m, 6H, CH3).

References: [1]Patent: US5677282,1997,A .

41
[ 943-80-6 ]
[ 501-53-1 ]
[ 14608-95-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; toluene;	(a) N-Benzyloxycarbonyl-p-benzyloxycarbonylamino-L-phenylalanine: 1.01 g of p-amino-L-phenylalanine (Bachem AG, Bubendorf) is taken up in the form of a sodium salt in 6 ml of H2 O. Then, while cooling with an ice bath, 3.35 ml of chloroformic acid benzyl ester (50% in toluene) and 5 ml of 2N NaOH are simultaneously added dropwise and the whole is then stirred for 20 minutes. The white suspension is adjusted to pH 1 with 2N HCl, extracted with ethyl acetate, and the organic phase is dried over sodium sulphate and concentrated by evaporation. The residue is purified by flash chromatography with solvent system B11. The elude is acidified with 2N HCl and extracted with ethyl acetate, and the extracts are dried and concentrated by evaporation to yield the title compound in the form of white crystals. Rf (B11)=0.22.

References: [1]Patent: US4727060,1988,A .

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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.: 943-80-6

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CAS No.: 943-80-6

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Product Details of 4-Amino-L-phenylalanine

Safety of 4-Amino-L-phenylalanine

Application In Synthesis of 4-Amino-L-phenylalanine

[ 943-80-6 ] Synthesis Path-Downstream 1~41

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