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Quality Control of Boc-Asp-OMe Purity: 97% SDS Specification

COA

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NMR

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CNMR

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Product Details of Boc-Asp-OMe

CAS No. :	98045-03-5
Formula :	C₁₀H₁₇NO₆
M.W :	247.25
SMILES Code :	O=C(O)C[C@H](NC(OC(C)(C)C)=O)C(OC)=O
MDL No. :	MFCD03094777
InChI Key :	IWFIVTBTZUCTQH-LURJTMIESA-N
Pubchem ID :	11021202

Safety of Boc-Asp-OMe

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

Application In Synthesis of Boc-Asp-OMe

* 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 [ 98045-03-5 ]

[ 98045-03-5 ] Synthesis Path-Downstream 1~35

1
[ 593-71-5 ]
[ 98045-03-5 ]
[ 70606-85-8 ]

References: [1]Journal of Medicinal Chemistry,1979,vol. 22,p. 657 - 661.

2
[ 67-56-1 ]
[ 13726-67-5 ]
[ 98045-03-5 ]

References: [1]Tetrahedron,1989,vol. 45,p. 741 - 748.
[2]Tetrahedron Letters,2014,vol. 55,p. 2274 - 2276.

3
[ 2577-90-4 ]
[ 98045-03-5 ]
methyl-3-(1-methoxycarbonyl-2-phenylethylcarbamoyl)-3-(t-butoxycarbonylamino)propanoate [ No CAS ]

References: [1]Journal of general chemistry of the USSR,1986,vol. 56,p. 1446 - 1449.
Zhurnal Obshchei Khimii,1986,vol. 56,p. 1631 - 1635.

4
[ 98045-03-5 ]
[ 530-62-1 ]
(S)-2-tert-Butoxycarbonylamino-4-imidazol-1-yl-4-oxo-butyric acid methyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 381 - 386.

5
Boc-Asp(OAll)-OMe [ No CAS ]
[ 98045-03-5 ]

References: [1]Tetrahedron Letters,1995,vol. 36,p. 5741 - 5744.

6
[ 196860-98-7 ]
[ 98045-03-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 8387 - 8393.

7
[ 98045-03-5 ]
2-<i>tert</i>-butoxycarbonylamino-3-isocyanato-propionic acid methyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1270 - 1280.

8
[ 98045-03-5 ]
[ 106-95-6 ]
2-allyl-2-<i>tert</i>-butoxycarbonylamino-succinic acid 1-methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2035 - 2040.

9
[ 98045-03-5 ]
[ 74-88-4 ]
[ 130622-08-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2035 - 2040.

10
[ 80963-12-8 ]
[ 98045-03-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With palladium 10% on activated carbon; hydrogen; In methanol; under 760.051 Torr; for 6h;Inert atmosphere;	Boc-L-aspartyl(OBn)(OMe) 14 (5.88 g, 17.43 mmol)was dissolved in MeOH (20 mL) in a 50 mL round bottom flask and 10% palladiumon carbon was added under nitrogen. The vessel was purged three times withnitrogen and three times with hydrogen. The mixture was then stirred for 6hours under hydrogen at atmospheric pressure. The catalyst was removed by filtration and thefiltrate was evaporated to obtain compound 15as a colorless gummy liquid. (4.1 g, 95%). [alpha]21D = 34 (c 0.1, CHCl3). 1HNMR: (CDCl3, 400 MHz) 1.43 (s, 9H), 2.83-2.86 (d, 1H, J = 16.92 Hz), 3.01-3.05 (d, 1H, J = 16.68 Hz), 3.74 (s, 3H), 4.57 (s,1H), 5.55-5.57 (d, 1H, J = 8.12 Hz),10.45 (s, 1H). 13C NMR: (CDCl3, 100 MHz) 28.3, 36.6, 49.7, 52.8, 80.5, 155.5, 171.5,176.0. IR (KBr) 3366, 2980, 1719, 1506, 1440, 1395, 1368, 1222, 1165,1060, 1008, 864, 764, 587 cm-1.
	With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; for 5h;Inert atmosphere;	Boc-Asp(OBn)-OH (600 mg, 1.85 mmol, 1.0 equiv) was added to a dried flask with a stir bar and dissolved in 3:1 toluene/MeOH (9 mL). The flask was fitted with a septum flushed with N2 and cooled to 0 C in an ice bath. Trimethylsilyl-diazomethane (2.0 M in diethyl ether) (1.39 mL, 2.78 mmol, 1.5 equiv) was added dropwise to the solution until the color of the solution turned yellow. The solution was allowed to stir for 20 mins and silica was added until the solution turned colorless again. The solution was filtered through celite, which was washed with MeOH. The product was concentrated under vacuum and dissolved in THF (15 mL) and a stir bar was added to the flask. 10% Pd on Carbon (231 mg, 125 mg/ mmol ester) was weighed into a vial capped with a septum then flushed with N2. THF (5 mL) was added and the slurry formed was transferred via pipette into the flask. The flask was capped with a septum and flushed with N2 and then flushed with H2 via balloon. The mixture was allowed to stir for 5 h under H2 then a 1H NMR spectra was taken to ensure complete debenzylation. The completed reaction was quenched by filtering through a pre-wetted pad of Celite which was rinsed with methanol. The resultant clear solution was concentrated by rotary evaporation, then again with hexanes yielding a fluffy white powder. The resultant powder was dried on high vacuum for two days. Analytical data collected were consistent with that previously reported.5
	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 3h;	Example 11: Preparation of (S)-2-(benzofuran-5-sulfonamido)-N,N-diisobutyl- 3-(2-methylthiazol-4-yl)propanamide (62); To a solution of Boc-L-Asp(Bzl)-OH (5.0 g, 15.5 mmol) in methanol (50 ml) was added diazomethane (7.8 ml, 15.5 mmol). The mixture was stirred for 1 hr at room temperature and concentrated in vacuo To a solution of the resulting compound in ethanol (50 ml) was added 10% palladium on charcoal and the mixture hydrogenated for 3 hrs at room temperature, filtered through Celite and concentrated in vacuo. The crude material was purified by flash column chromatography (30% EtOAc in hexanes) to provide compound 231 (2.6 g, 69%) as a white solid. Compound 232 (2.0 g, 65%, colorless oil) was prepared as described in Journal of Medicinal Chemistry, 2007, Vol. 50, No. 8, 1850- 1864.To a solution of compound 232 (200 mg, 0.62 mmol) in EtOH (4 ml) was added thioacetamide (40 mul, 0.68 mmol) and the resulting mixture refluxed at 90 0C. After 16 hrs, the mixture was concentrated in vacuo. The residue was purified by preparative TLC (50% <n="77"/>EtOAc in hexanes) to provide compound 233 (100 mg, 53%) as a yellowish oil. [M+H]+ 301.0, HPLC purity: 90%.To a solution of compound 233 (100 mg, 0.33 mmol) in tetrahydrofuran/MeOH (3:1, 5 ml) was added lithium hydroxide in water (2.5 M, 0.15 ml, 0.36 mmol). The mixture was stirred for 3 hrs at room temperature, quenched with aqueous IN HCl (5 ml), and extracted with EtOAc (7 ml). The organic phase was washed with brine (5 ml), dried over anhydrous MgSO4 and concentrated in vacuo. To a solution of the residue in DMF (2 ml) were added diisobutylamine (57 mul, 0.33 mmol), DIPEA (0.17 ml, 0.99 mmol), and TBTU (159 mg, 0.49 mmol). The mixture was stirred for 1 hr at room temperature, quenched with saturated aqueous sodium bicarbonate (7 ml) and extracted with EtOAc (7 ml). The organic phase was washed with brine (10 ml), dried over anhydrous MgSO4 and concentrated in vacuo. The crude material was purified by preparative TLC (50% EtOAc in hexanes) to provide compound 234 (83 mg, 64%) as a colorless oil. [M+H]+ 398.3, HPLC purity: 99%. To a solution of compound 234 (83 mg, 0.21 mmol) in dichloromethane (2 ml) was added 4N HCl in dioxane (2 ml). The mixture was stirred for 1 hr at room temperature and concentrated in vacuo. To a solution of the resulting material in dichloromethane (4 ml) were added triethylamine (88 mul, 0.63 mmol) and benzofuran-5-sulfonyl chloride (68 mg, 0.32 mmol). After 30 min, water (4 ml) was added to quench the reaction. The aqueous phase was extracted with dichloromethane (5 ml) and the organic layer was washed with brine (4 ml), dried over anhydrous MgSO4 and concentrated in vacuo. The crude material was purified by preparative TLC (50% EtOAc in hexanes) to provide compound 62 (45 mg, 45%) as a white solid. [M+H]+ 478.0, [2M+Na]+ 977.2, HPLC purity: 99%.

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1459 - 1465.
[2]Tetrahedron Letters,2014,vol. 55,p. 2274 - 2276.
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 15 - 20.
[4]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 586 - 590.
[5]Carbohydrate Research,2013,vol. 382,p. 36 - 42.
[6]Patent: WO2009/105774,2009,A2 .Location in patent: Page/Page column 75-76.

11
[ 98045-03-5 ]
[ 107-11-9 ]
[ 709674-74-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 15 - 20.

12
[ 51987-73-6 ]
[ 98045-03-5 ]

References: [1]Synthesis,2005,p. 933 - 938.

13
[ 98045-03-5 ]
[ 6205-69-2 ]
[ 98045-02-4 ]

References: [1]Carbohydrate Research,2006,vol. 341,p. 1574 - 1596.

14
2-hydroxybenzotriazole [ No CAS ]
[ 98045-03-5 ]
C₁₆H₂₀O₆N₄ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1459 - 1465.

15
[ 98045-03-5 ]
[ 120042-11-7 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

16
[ 98045-03-5 ]
[ 543-27-1 ]
CO₂CH₃CHNHCO₂C₄H₉CH₂CO₂COC₄H₉O [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

17
[ 2033-24-1 ]
[ 98045-03-5 ]
CO₂CH₃CHNHCO₂C₄H₉CH₂COHC₆H₆O₄ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

18
[ 6066-82-6 ]
[ 98045-03-5 ]
C₁₄H₂₀N₂O₈ [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 4423 - 4426.

19
[ 98045-03-5 ]
[ 955376-02-0 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

20
[ 98045-03-5 ]
[ 955376-03-1 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

21
[ 98045-03-5 ]
C₆₀H₇₄N₂O₁₃H₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

22
[ 98045-03-5 ]
(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

23
[ 98045-03-5 ]
C₆₀H₇₄N₂O₁₃H₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

24
[ 98045-03-5 ]
(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

25
[ 98045-03-5 ]
C₆₀H₇₄N₂O₁₃H₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

26
[ 98045-03-5 ]
(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

27
[ 98045-03-5 ]
C₆₀H₇₄N₂O₁₃H₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

28
[ 98045-03-5 ]
(2'''S)-2-((2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)methyl)-4-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

29
[ 98045-03-5 ]
C₆₀H₇₄N₂O₁₃H₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

30
[ 98045-03-5 ]
(2'''S)-2-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-4-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

31
[ 98045-03-5 ]
C₆₀H₇₄N₂O₁₃H₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

32
[ 98045-03-5 ]
(2'''S)-2-((2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)methyl)-4-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

33
[ 98045-03-5 ]
C₆₀H₇₄N₂O₁₃H₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

34
[ 98045-03-5 ]
(2'''S)-2-((2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)methyl)-4-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

35
[ 98045-03-5 ]
[ 955376-11-1 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 7677 - 7687.

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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.: 98045-03-5

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CAS No.: 98045-03-5

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[ 98045-03-5 ] Synthesis Path-Downstream 1~35

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