Boc-Tyr-OtBu | Carbamates

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Quality Control of Boc-Tyr-OtBu Purity: 98% SDS Specification

COA

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NMR

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Product Details of Boc-Tyr-OtBu

CAS No. :	18938-60-8
Formula :	C₁₈H₂₇NO₅
M.W :	337.41
SMILES Code :	O=C(OC(C)(C)C)[C@@H](NC(OC(C)(C)C)=O)CC1=CC=C(O)C=C1
MDL No. :	MFCD20264826
InChI Key :	WGJGINMQCMATNP-AWEZNQCLSA-N
Pubchem ID :	15512828

Safety of Boc-Tyr-OtBu

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

Application In Synthesis of Boc-Tyr-OtBu

* 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 [ 18938-60-8 ]

[ 18938-60-8 ] Synthesis Path-Downstream 1~35

1
[ 1070-19-5 ]
[ 16874-12-7 ]
[ 18938-60-8 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1968,vol. 4,p. 942 - 945.
Zhurnal Organicheskoi Khimii,1968,vol. 4,p. 971 - 975.

2
[ 24529-88-2 ]
[ 18938-60-8 ]
O-<L-α-(α',β-Dioleyl)-glyceryl-phosphoryl>-L-tyrosin [ No CAS ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1968,vol. 4,p. 942 - 945.
Zhurnal Organicheskoi Khimii,1968,vol. 4,p. 971 - 975.

3
[ 98946-18-0 ]
[ 3978-80-1 ]
[ 18938-60-8 ]
[ 158008-98-1 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 1557 - 1560.

4
[ 18938-60-8 ]
[ 200502-01-8 ]
[ 312750-63-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 3003 - 3006.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 4570 - 4574.
[3]Nucleosides, nucleotides and nucleic acids,2001,vol. 20,p. 315 - 321.

6
[ 3978-80-1 ]
[ 75-65-0 ]
[ 18938-60-8 ]

References: [1]Nucleosides, nucleotides and nucleic acids,2001,vol. 20,p. 315 - 321.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 4570 - 4574.
[3]Chemistry - An Asian Journal,2011,vol. 6,p. 1316 - 1320.

7
[ 18938-60-8 ]
[ 3978-80-1 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 4921 - 4924.
[2]Journal of Organic Chemistry,2001,vol. 66,p. 4430 - 4432.

8
[ 358-23-6 ]
[ 18938-60-8 ]
[ 174003-17-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 0℃; for 4h;	To a solution of 18.5 g (55 mmol) of N-(Boc)-L-tyrosine, t-butyl ester (Reference Example 3, Step A) in 150 ml of dry methylene chloride was added 17.4 g (220 mmol) of pyridine followed at 0 C. by the addition of 18.6 g (66 mmol) of triflic anhydride neat dropwise. The reaction mixture was stirred at 0 C. and monitored by TLC. After 4 hours the mixture was diluted with 200 ml of methylene chloride and was washed with 1N HCl (3×100 ml), saturated sodium bicarbonate (2×100 ml) and brine (1×50 ml). The solution was dried over MgSO4, filtered and concentrated in vacuo to give an oil. The oil was dissolved in a mixture of 125 ml of toluene and 61 ml of ethanol. To this solution was added 11.3 g (62 mmol) of 2,6-dimethoxyboronic acid and 2.5 g of palladium tetrakistriphenylphosphine. The solution was treated with 18.3 g (133 mmol) of potassium carbonate dissolved in 30 ml of water. The mixture was heated to reflux over 4 hours, diluted with 200 ml of ethyl acetate and was washed with water (3×75 ml), brine (1×75 ml) and was dried over MgSO4. The mixture was filtered and concentrated in vacuo and the residue was purified by flash chromatography over silica gel eluted with a gradient of 5-20% EtOAc/hexanes to provide 14.7 g of N-(Boc)-(L)-4-(2',6'-dimethoxyphenyl)phenylalanine, t-butyl ester as a white solid. The solid was dissolved in 350 ml of t-butyl acetate at 0 C. and was treated with 8.3 ml of concentrated sulfuric acid. The cold bath was removed and after one hour TLC indicated only starting material was present. The reaction mixture was cooled in an ice bath once more and treated with 3.4 ml of concentrated sulfuric acid. The reaction was monitored by TLC. After consumption of the starting material the reaction mixture was diluted with 300 ml of ethyl acetate and was washed with 3×100 ml of 1N NaOH followed by brine (1×100 ml). The solution was dried over MgSO4. Filtered and was concentrated in vacuo to provide 8.9 g of (L)-4-(2',6'-dimethoxyphenyl)phenylalanine, t-butyl ester. 500 MHz 1H NMR (CD3OD): delta1.45 (s, 9H), 3.20 (d, 2H); 3.69 (s, 6H); 4.20 (t, 1H); 6.72 (d, 2H), 7.15 (m, 5H).

References: [1]Patent: US6713514,2004,B1 .Location in patent: Page/Page column 9-10.
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 729 - 731.
[3]Patent: US6353099,2002,B1 .Location in patent: Page column 29.

9
[ 24424-99-5 ]
L-tyrosine tert-butyl ester hydrochloride [ No CAS ]
[ 18938-60-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 729 - 731.

10
[ 14660-52-7 ]
[ 18938-60-8 ]
[ 859170-42-6 ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

11
[ 105-36-2 ]
[ 18938-60-8 ]
2-tert-butoxycarbonylamino-3-(4-ethoxycarbonylmethoxy-phenyl)-propionic acid tert-butyl ester [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

12
[ 61699-62-5 ]
[ 18938-60-8 ]
2-tert-butoxycarbonylamino-2-(1-hydroxy-2,3-diisopropoxy-4-oxo-cyclobut-2-enyl)-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 311 - 314.

13
[ 3355-28-0 ]
[ 18938-60-8 ]
[ 827036-34-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 15h;	To an anhydrous N,N-dimethylformamide solution (2.0 mL) of N-t-butoxycarbonyl-L-tyrosine-t-butyl ester (338 mg, 1.0 mM), potassium carbonate (173 mg, 1.25 mM) and 1-bromo-2-butyne (147 mg, 1.1 mM) were added, followed by stirring at room temperature for 15 hours. Ethyl acetate (30 mL) was added to the reaction solution, followed by washing three times with water (20 mL) and with brine (20 mL) sequentially. The ethyl acetate layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Subsequently, the resulting oily substance was purified by silica gel column chromatography. From n-hexane/ethyl acetate (5:1) eluted fraction, Compound 48 (370 mg, 95%) was obtained as a colorless oily substance. Physicochemical property of Compound 48 Molecular weight: 389 FAB-MS (positive mode, matrix m-NBA) 390 (M+H+) 1H-NMR Chemical shift value delta (in deuterated chloroform): 1.41 (9H, s), 1.42 (9H, s), 1.86 (3H, t, J=2.5Hz), 3.00 (2H, d, J=6.0Hz), 4.41 (1H, dd, J=7.5, 6.0Hz), 4.62 (2H, q, J=2.5Hz), 4.97 (1H, d, J=7.5Hz), 6.88 (2H, d, J=8.5Hz), 7.08 (2H, d, J=8.5Hz)

References: [1]Patent: EP1857456,2007,A1 .Location in patent: Page/Page column 64-65.
[2]Organic Process Research and Development,2018,vol. 22,p. 236 - 240.

14
[ 18938-60-8 ]
[ 839718-58-0 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 311 - 314.

15
[ 18938-60-8 ]
[ 244614-32-2 ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

16
[ 18938-60-8 ]
[ 680209-40-9 ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

17
[ 18938-60-8 ]
[ 680209-39-6 ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

18
[ 18938-60-8 ]
N-Boc-Tyr-[O(CH₂)4CON₃]-OtBu [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

19
[ 18938-60-8 ]
[ 680209-55-6 ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

20
[ 18938-60-8 ]
[ 680209-56-7 ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

21
[ 18938-60-8 ]
2-tert-butoxycarbonylamino-3-(4-{4-[1-(3-tert-butylcarbamoyl-octahydro-isoquinolin-2-ylmethyl)-2-(3-hydroxy-2-methyl-benzoylamino)-3-phenylsulfanyl-propoxycarbonylamino]-butoxy}-phenyl)-propionic acid tert-butyl ester [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

22
[ 18938-60-8 ]
[ 680209-72-7 ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

23
[ 18938-60-8 ]
5-[4-(2-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-phenoxy]-pentanoic acid 1-(3-tert-butylcarbamoyl-octahydro-isoquinolin-2-ylmethyl)-2-{3-carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-3-phenyl-propyl ester [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

24
[ 18938-60-8 ]
2-tert-butoxycarbonylamino-3-{4-[4-(1-(3-tert-butylcarbamoyl-octahydro-isoquinolin-2-ylmethyl)-2-{3-carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-3-phenyl-propoxycarbonylamino)-butoxy]-phenyl}-propionic acid tert-butyl ester [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

25
[ 18938-60-8 ]
(S)-2-Amino-3-(4-{(1S,2R)-1-[(2R,4S)-2-benzyl-5-((S)-2-tert-butylcarbamoyl-4-pyridin-3-ylmethyl-piperazin-1-yl)-4-hydroxy-pentanoylamino]-indan-2-yloxycarbonylmethoxy}-phenyl)-propionic acid; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

26
[ 18938-60-8 ]
(S)-2-Amino-3-{4-[(1S,3R)-1-((S)-2-tert-butylcarbamoyl-4-pyridin-3-ylmethyl-piperazin-1-ylmethyl)-3-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-4-phenyl-butoxycarbonylmethoxy]-phenyl}-propionic acid; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

27
[ 18938-60-8 ]
(S)-2-Amino-3-(4-{4-[(1R,2R)-1-((3S,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-ylmethyl)-2-(3-hydroxy-2-methyl-benzoylamino)-3-phenylsulfanyl-propoxycarbonylamino]-butoxy}-phenyl)-propionic acid; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

28
[ 18938-60-8 ]
(S)-2-Amino-3-(4-{4-[(1S,3R)-1-((S)-2-tert-butylcarbamoyl-4-pyridin-3-ylmethyl-piperazin-1-ylmethyl)-3-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-4-phenyl-butoxycarbonylamino]-butoxy}-phenyl)-propionic acid; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

29
[ 18938-60-8 ]
5-[4-((S)-2-Amino-2-carboxy-ethyl)-phenoxy]-pentanoic acid (1R,2S)-1-((3S,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-ylmethyl)-2-{(S)-3-carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-3-phenyl-propyl ester; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

30
[ 18938-60-8 ]
[ 680209-57-8 ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

31
[ 18938-60-8 ]
(S)-2-Amino-3-{4-[4-((1R,2S)-1-((3S,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-ylmethyl)-2-{(S)-3-carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-3-phenyl-propoxycarbonylamino)-butoxy]-phenyl}-propionic acid; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

32
[ 18938-60-8 ]
(S)-2-Amino-3-(4-{(1S,2R)-1-[(2R,4S)-4-{2-[4-((S)-2-amino-2-carboxy-ethyl)-phenoxy]-acetoxy}-2-benzyl-5-((S)-2-tert-butylcarbamoyl-4-pyridin-3-ylmethyl-piperazin-1-yl)-pentanoylamino]-indan-2-yloxycarbonylmethoxy}-phenyl)-propionic acid; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Organic and biomolecular chemistry,2004,vol. 2,p. 345 - 357.

33
[ 18938-60-8 ]
3-(2',6'-dimethoxy-biphenyl-4-yl)-2-(pyridin-2-ylamino)-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 729 - 731.

34
[ 18938-60-8 ]
3-(2',6'-dimethoxy-biphenyl-4-yl)-2-phenylamino-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 729 - 731.

35
[ 18938-60-8 ]
3-(2',6'-dimethoxy-biphenyl-4-yl)-2-(pyridin-4-ylamino)-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 729 - 731.

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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.: 18938-60-8

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CAS No.: 18938-60-8

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Application In Synthesis of Boc-Tyr-OtBu

[ 18938-60-8 ] Synthesis Path-Downstream 1~35

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