[ CAS No. 198474-90-7 ] {[proInfo.proName]}

Name: 198474-90-7|Boc-Phe(3,4-DiF)-OH|97%
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SKU: A102246
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Quality Control of [ 198474-90-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 198474-90-7 ]

SDS Specification

Alternatived Products of [ 198474-90-7 ]

Product Details of [ 198474-90-7 ]

CAS No. :	198474-90-7	MDL No. :	MFCD00672518
Formula :	C₁₄H₁₇F₂NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CYAOPVHXASZUDE-NSHDSACASA-N
M.W :	301.29	Pubchem ID :	7020829
Synonyms :	(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(3,4-difluorophenyl)propionic acid	Chemical Name :	Boc-Phe(3,4-DiF)-OH

Calculated chemistry of [ 198474-90-7 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.43
Num. rotatable bonds :	7
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	71.26
TPSA :	75.63 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) :	-6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	2.71
Log Po/w (WLOGP) :	3.33
Log Po/w (MLOGP) :	2.76
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	2.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.16
Solubility :	0.206 mg/ml ; 0.000684 mol/l
Class :	Soluble
Log S (Ali) :	-3.95
Solubility :	0.0337 mg/ml ; 0.000112 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.72
Solubility :	0.057 mg/ml ; 0.000189 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.93

Safety of [ 198474-90-7 ]

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

Application In Synthesis of [ 198474-90-7 ]

* 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 [ 198474-90-7 ]
Downstream synthetic route of [ 198474-90-7 ]

[ 198474-90-7 ] Synthesis Path-Upstream 1~4

1
[ 15017-45-5 ]
[ 198474-90-7 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 6, p. 923 - 927

2
[ 85118-01-0 ]
[ 198474-90-7 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 6, p. 923 - 927

3
[ 266360-51-4 ]
[ 198474-90-7 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 6, p. 923 - 927

4
[ 24424-99-5 ]
[ 31105-90-5 ]
[ 198474-90-7 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 6, p. 923 - 927

[ 198474-90-7 ] Synthesis Path-Downstream 1~51

1
[ 24424-99-5 ]
[ 31105-90-5 ]
[ 198474-90-7 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 923 - 927

2
[ 2592-95-2 ]
[ 198474-90-7 ]
2-tert-butoxycarbonylamino-3-(3,4-difluoro-phenyl)-propionic acid benzotriazol-1-yl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2363 - 2367
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 4043 - 4049

3
[ 198474-90-7 ]
[ 1117-97-1 ]
[ 949912-52-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5176 - 5181

4
[ 198474-90-7 ]
[ 949912-56-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5176 - 5181

5
[ 198474-90-7 ]
(S)-2-Amino-3-methyl-butyric acid (S)-2-amino-3-(3,4-difluoro-phenyl)-1-ethylcarbamoyl-propyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5176 - 5181

6
[ 198474-90-7 ]
[ 949912-99-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5176 - 5181

7
[ 198474-90-7 ]
2-tert-butoxycarbonylamino-3-methyl-butyric acid 2-tert-butoxycarbonylamino-3-(3,4-difluoro-phenyl)-1-ethylcarbamoyl-propyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5176 - 5181

8
[ 198474-90-7 ]
5-[1,2]Dithiolan-3-yl-pentanoic acid {(S)-1-[(S)-1-(3,4-difluoro-benzyl)-2-ethylcarbamoyl-2-oxo-ethylcarbamoyl]-2-methyl-propyl}-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5176 - 5181

9
[ 198474-90-7 ]
[ 949913-02-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5176 - 5181

10
[ 198474-90-7 ]
[ 603137-53-7 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4043 - 4049
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2363 - 2367

11
[ 198474-90-7 ]
(R)-N-{(S)-2-(3,4-Difluoro-phenyl)-1-[(S)-4-guanidino-1-(thiazole-2-carbonyl)-butylcarbamoyl]-ethyl}-3-phenyl-2-phenylmethanesulfonylamino-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4043 - 4049
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2363 - 2367

12
[ 198474-90-7 ]
C₂₈H₃₆F₂N₆O₅S₂*ClH [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4043 - 4049
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2363 - 2367

13
[ 198474-90-7 ]
[ 603137-79-7 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4043 - 4049
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2363 - 2367

14
[ 198474-90-7 ]
C₄₄H₅₁F₂N₇O₈S₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4043 - 4049
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2363 - 2367

15
[ 15017-45-5 ]
[ 198474-90-7 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 923 - 927

16
[ 85118-01-0 ]
[ 198474-90-7 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 923 - 927

17
[ 266360-51-4 ]
[ 198474-90-7 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 923 - 927

18
2-acetylamino-2-(3,4-difluoro-benzyl)-malonic acid [ No CAS ]
[ 198474-90-7 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 923 - 927

19
[ 198474-90-7 ]
[ 343566-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In 1,4-dioxane; sulfuric acid;	Preparation of Intermediate (2R)-3-(3',4'-Difluorophenyl)-2-hydroxypropionic Acid <strong>[198474-90-7]Boc-D-3,4-Difluorophenylalanine</strong> (3.05 g, 11.0 mmol, 1 equiv) was dissolved in 1,4-dioxane (10 mL), and a solution of HCl in 1,4-dioxane (4.0 M, 10 mL) was added. The reaction was stirred at 23 C. for 5 h, then the solvent was removed under reduced pressure. The residue was dissolved in 1 M H2SO4 (22 mL), cooled to 0 C. and 2 N NaNO2 (22 mL) was added via addition funnel under argon. The reaction mixture was stirred at 0 C. for 3 h and warmed to room temperature overnight. The resulting mixture was extracted with MTBE (3*40 mL), dried over Na2SO4 and concentrated. The residue was recrystallized from ether/petroleum ether to afford the title intermediate (1.29 g, 58%) as off-white solid. 1H NMR (DMSO-d6) delta 0.82-0.86 (m, 2H), 1.10-1.27 (m, 4H), 1.40-1.48 (m, 2H), 1.63-1.78 (m, 5H), 3.95-4.00 (m, 1H).

Reference： [1]Patent: US2001/47006,2001,A1

20
2-amino-5-aminomethylpyridine dihydrochloride [ No CAS ]
[ 198474-90-7 ]
[ 1194096-58-6 ]

Yield	Reaction Conditions	Operation in experiment
88%		B. [(S)-l-[(6-Amino-pyridin-3-ylmethyl)-carbamoyll-2-(3,4-difluoro-phenyI)-ethylI- carbamic acid tert-butyl esterBoc-3,4-difluoro-Phe-OH (5.0g, 16.6mmol) was dissolved in CH2Cl2(100mls) and DMF (lOmls). This solution was cooled to 0 C. 5-aminomethyI-pyridin-2-ylamine dihydrochloride (3.58g, 18.2mmol) was added followed by HOBt (2.69g, 19.9mmol) and water soluble carbodiimide (3.18g, 16.6mmol). After 15mins diisopropylethylamine (6.44g, 49.8mmol) was added. After 5 hrs at 0 C to room temperature the reaction mixture was diluted with CHC13 (150mls), this solution was washed with sat. NaHC03 (lx50mls), water (lx50mls), brine (lx50mls), dried (Na2S04) and evaporated in vacuo. The residue was purified by flash chromatography (silica), eluent 5%MeOH, 95% CHCI3, fractions combined and evaporated in vacuo to give a yellow oil identified as the title compound.Yield = 5.79g, 14.2mmol, 88%[M+H]+ = 407.16
88%		Boc-3,4-difluoro-Phe-OH (5.0g, 16.6mmol) was dissolved in CH2Cl2(IOOmIs) and DMF (1 OmIs). This solution was cooled to O0C. 5-Aminomethyl-pyridin-2-ylamine dihydrochloride (3.58g, 18.2mmol) was added followed by HOBt (2.69g, 19.9mmol) and water soluble carbodiimide (3.18g, 16.6mmol). After 15mins diisopropylethylamine (6.44g, 49.8mmol) was added. After 5 hrs O0C to room temperature the reaction mixture was diluted with CHCl3 (15OmIs), this solution was washed with sat. NaHCO3 <n="84"/>(lx50mls), water (lx50mls), brine (lx50mls), dried (Na2SO4) and evaporated in vacuo.The residue was purified by flash chromatography (silica), eluent 5%MeOH, 95% CHCl3, fractions combined and evaporated in vacuo to give a yellow oil identified as the title compound. Yield = 5.79g, 14.2mmol, 88% [M+H]+ = 407.16

Reference： [1]Patent: WO2011/51671,2011,A1 .Location in patent: Page/Page column 60-61
[2]Patent: WO2009/133348,2009,A1 .Location in patent: Page/Page column 82-83

21
[ 885223-59-6 ]
[ 198474-90-7 ]
C₂₄H₂₄F₂N₆O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1652 - 1656

22
[ 198474-90-7 ]
[ 1239576-61-4 ]

Yield	Reaction Conditions	Operation in experiment
74%		Preparation 1; Preparation of 2-[(2S)-2-amino-3-(3,4-difluorophenyl)propyl1-1 /-/-isoindole-1 ,3(2H)-dione; a) 1 ,1-dimethylethyl [(1 S)-2-(3,4-difluorophenyl)-1-(hydroxymethyl)ethyl]carbamate; To a solution of Lambda/-[(1 ,1-dimethylethyl)oxy]carbonyl}-3,4-difluoro-L-phenylalanine (2.0 g, 6.7 mmol) in THF (35 ml.) at 0 0C stirred was added BH3-THF (30 ml_, 30 mmol- 1 M in THF). After 12h, the reaction was quenched with AcOH:MeOH (1 :4, 20 ml.) and partitioned between saturated aqueous NaHCO3 and CHCI3. The aqueous phase was then extracted several times with CHCI3. The combined organic fractions were concentrated and the resulting white solid (7.0 g, 74%) used without further purification: LCMS (ES) m/e 288 (M+H)+.

Reference： [1]Patent: WO2010/93885,2010,A1 .Location in patent: Page/Page column 35-36

23
[ 267876-25-5 ]
[ 198474-90-7 ]
[ 1300197-90-3 ]