[ CAS No. 17791-52-5 ] {[proInfo.proName]}

Name: 17791-52-5|Boc-His-OH|98%
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Quality Control of [ 17791-52-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17791-52-5 ]

SDS Specification

Alternatived Products of [ 17791-52-5 ]

Product Details of [ 17791-52-5 ]

CAS No. :	17791-52-5	MDL No. :	MFCD00065576
Formula :	C₁₁H₁₇N₃O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AYMLQYFMYHISQO-QMMMGPOBSA-N
M.W :	255.27	Pubchem ID :	87308
Synonyms :	N-tert-Butyloxycarbonyl-L-histidine	Chemical Name :	Boc-His-OH

Calculated chemistry of [ 17791-52-5 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.55
Num. rotatable bonds :	7
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	63.49
TPSA :	104.31 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	0.69
Log Po/w (WLOGP) :	0.93
Log Po/w (MLOGP) :	-0.41
Log Po/w (SILICOS-IT) :	0.6
Consensus Log Po/w :	0.68

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.6
Solubility :	6.4 mg/ml ; 0.0251 mol/l
Class :	Very soluble
Log S (Ali) :	-2.46
Solubility :	0.89 mg/ml ; 0.00349 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.02
Solubility :	2.45 mg/ml ; 0.00959 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.99

Safety of [ 17791-52-5 ]

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

Application In Synthesis of [ 17791-52-5 ]

* 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 [ 17791-52-5 ]
Downstream synthetic route of [ 17791-52-5 ]

[ 17791-52-5 ] Synthesis Path-Upstream 1~16

1
[ 17791-52-5 ]
[ 32926-43-5 ]

Reference： [1] Chemistry of Natural Compounds, 1982, vol. 18, # 3, p. 322 - 327[2] Khimiya Prirodnykh Soedinenii, 1982, # 3, p. 349 - 354

2
[ 596-43-0 ]
[ 17791-52-5 ]
[ 32926-43-5 ]

Reference： [1] Chemistry of Natural Compounds, 1982, vol. 18, # 3, p. 322 - 327[2] Khimiya Prirodnykh Soedinenii, 1982, # 3, p. 349 - 354

3
[ 83468-83-1 ]
[ 17791-52-5 ]

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 2, p. 311 - 313

4
[ 50305-43-6 ]
[ 17791-52-5 ]

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 2, p. 311 - 313

5
[ 24424-99-5 ]
[ 71-00-1 ]
[ 17791-52-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3150 - 3154
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3150 - 3154
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 15, p. 6607 - 6621

6
[ 24424-99-5 ]
[ 1007-42-7 ]
[ 17791-52-5 ]

Reference： [1] RSC Advances, 2016, vol. 6, # 48, p. 41951 - 41961

7
[ 1604-44-0 ]
[ 17791-52-5 ]

Reference： [1] RSC Advances, 2016, vol. 6, # 48, p. 41951 - 41961
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 15, p. 6607 - 6621

8
[ 4467-54-3 ]
[ 17791-52-5 ]

Reference： [1] RSC Advances, 2016, vol. 6, # 48, p. 41951 - 41961

9
[ 24424-99-5 ]
[ 17791-52-5 ]

Reference： [1] Chemistry of Natural Compounds, 1982, vol. 18, # 3, p. 322 - 327[2] Khimiya Prirodnykh Soedinenii, 1982, # 3, p. 349 - 354

10
[ 84553-13-9 ]
[ 17791-52-5 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 8, p. 2766 - 2779

11
[ 5934-29-2 ]
[ 58632-95-4 ]
[ 17791-52-5 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 11, p. 3112 - 3113

12
[ 20866-46-0 ]
[ 870-46-2 ]
[ 17791-52-5 ]

Reference： [1] Chemistry of Natural Compounds, 1982, vol. 18, # 3, p. 322 - 327[2] Khimiya Prirodnykh Soedinenii, 1982, # 3, p. 349 - 354

13
[ 58632-95-4 ]
[ 71-00-1 ]
[ 17791-52-5 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 10, p. 779 - 782

14
[ 98-59-9 ]
[ 17791-52-5 ]
[ 35899-43-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 17, p. 2431 - 2447

15
[ 17791-52-5 ]
[ 24305-27-9 ]

Reference： [1] Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 5, p. 5324 - 5332

16
[ 20866-46-0 ]
[ 870-46-2 ]
[ 17791-52-5 ]

Reference： [1] Chemistry of Natural Compounds, 1982, vol. 18, # 3, p. 322 - 327[2] Khimiya Prirodnykh Soedinenii, 1982, # 3, p. 349 - 354

[ 17791-52-5 ] Synthesis Path-Downstream 1~22

1
[ 5934-29-2 ]
[ 58632-95-4 ]
[ 17791-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	With Dowex 50; triethylamine 1.) H₂O, dioxane, 5 h, pH=8; 2.) MeOH, 0.1M pyridinium acetate buffer; Yield given. Multistep reaction;

Reference： [1]Kawasaki; Miyano; Murakami; Kakimi [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 11, p. 3112 - 3113]

2
[ 98-59-9 ]
[ 17791-52-5 ]
[ 35899-43-5 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2431 - 2447

3
[ 596-43-0 ]
[ 17791-52-5 ]
[ 32926-43-5 ]

Reference： [1]Chemistry of Natural Compounds,1982,vol. 18,p. 322 - 327
Khimiya Prirodnykh Soedinenii,1982,p. 349 - 354

4
[ 19887-32-2 ]
[ 104882-10-2 ]
[ 17791-52-5 ]
{(S)-1-[(S)-1-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2264 - 2276

5
[ 19887-32-2 ]
[ 117248-32-5 ]
[ 17791-52-5 ]
{(S)-1-[(S)-1-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-pentylcarbamoyl)-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2264 - 2276

6
[ 55447-00-2 ]
[ 104882-10-2 ]
[ 17791-52-5 ]
{(S)-1-[(S)-1-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2264 - 2276

7
[ 80745-07-9 ]
[ 17791-52-5 ]
[ 84552-49-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1982,vol. 30,p. 2766 - 2779

8
[ 67-56-1 ]
[ 17791-52-5 ]
[ 2488-14-4 ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 8401 - 8404

9
[ 50305-43-6 ]
[ 17791-52-5 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 311 - 313

10
[ 7524-50-7 ]
[ 17791-52-5 ]
methyl (tert-butoxycarbonyl)-L-histidyl-L-phenylalaninate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h;
70%	With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; Cooling with ice;	Boc(L)His-PheOMe: To an ice cooled mixture of Boc(L)His-OH (1.0 equiv.) in DMF, DCC (1.1 equiv.),HOBtH2O (1.1 equiv.), DIPEA (2.2 equiv.) and HClNH2Phe-OMe (1.0 equiv.) were added underanhydrous conditions. The mixture was stirred for 20 min and then was left to warm at roomtemperature (r.t.) overnight. The solvent was evaporated under reduced pressure and the solid residuewas crystallized from EtOAc. All the collected organic phases were evaporated under reduced pressure. The residue was dissolved in EtOAc/1-butanol (2:1, v:v) and washed with 5% citric acid (three times),NaHCO3 s.s. (three times) and brine (three times). The organic phase was dried on anhydrous Na2SO4,filtered and the solvent removed under reduced pressure to give the crude product which was purifiedby silica gel column chromatography (gradient from CHCl3/MeOH = 97:3 to CHCl3/MeOH = 93:7,v:v) to obtain the final product in 70% yield. 1H-NMR (300 MHz, DMSO-d6) d: 1.30 (s, 9H, Boc-His),2.61-2.74 (m, 2H, Phe-CH2), 2.86-2.99 (m, 2H, His-CH2), 3.54 (s, 3H, Phe-OCH3), 4.10-4.14 (m, 1H,His-CH), 4.43-4.47 (m, 1H, Phe-CH), 6.69 (t, 1H, Boc-NH), 6.84 (d, 1H, CCHNH), 7.17-7.27 (m, 5H,Phe aromatic ring), 7.51 (d, 1H, amide), 8.18 (d, 1H, NCHNH).
	With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 16h;

With triethylamine; dicyclohexyl-carbodiimide

Reference： [1]Chan, Hwai-Chien; Bueno, Bianca; Le Roch, Adrien; Gagnon, Alexandre [Chemistry - A European Journal, 2021, vol. 27, # 53, p. 13330 - 13336]
[2]Mollica, Adriano; Macedonio, Giorgia; Stefanucci, Azzurra; Carradori, Simone; Akdemir, Atilla; Angeli, Andrea; Supuran, Claudiu T. [Molecules, 2017, vol. 22, # 12]
[3]Orain, David; Koch, Guido; Giger, Rudolf [Chimia, 2003, vol. 57, # 5, p. 255 - 261]
[4]Dahiya, Rajiv; Kumar, Anil; Yadav, Rakesh [Molecules, 2008, vol. 13, # 4, p. 958 - 976]

11
[ 17791-52-5 ]
[ 32926-43-5 ]

Reference： [1]Chemistry of Natural Compounds,1982,vol. 18,p. 322 - 327
Khimiya Prirodnykh Soedinenii,1982,p. 349 - 354

12
[ 17791-52-5 ]
[ 7531-52-4 ]
[ 29133-55-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: N-(tert-butoxycarbonyl)-L-histidine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 25℃; for 2h; Stage #2: L-prolinamide In N,N-dimethyl-formamide at 25℃; for 18h;	7.13.1 To a solution of Nα-(tert-butoxycarbonyl)-L-histidine (0.5 g, 1.96 mmol) in DMF (10 mL) were added DCC (0.44 g, 2.15 mmol, 1.1 equiv) and HOBt (0.34 g, 2.15 mmol, 1.1 equiv). The resulting mixture was stirred at 25° C. for 2 h. L-ProNH2 (0.23 g, 2.01 mmol, 1.03 equiv) was added and the mixture stirred at 25° C. for an additional 18 h. The white residue was filtered off and the clear solution concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (CHCl3/MeOH/NH3 40/10/1) to afford the title compound (0.70 g, 73%) as a white solid: mp 97-101° C.; 1H NMR (CDCl3) δ 1.44 (s, 9H), 1.86-2.08 (m, 2H), 2.09-2.26 (m, 2H), 3.00-3.16 (m, 2H), 3.20-3.38 (m, 1H), 3.60-3.70 (m, 1H), 4.51 (t, 1H, J=6.6 Hz), 4.57-4.70 (m, 1H), 5.59 (br s, 1H), 6.20 (br s, 1H), 6.84 (s, 1H), 7.42 (s, 1H).
	Stage #1: N-(tert-butoxycarbonyl)-L-histidine With HONB; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 0.25h; Stage #2: L-prolinamide In N,N-dimethyl-formamide at 20℃;	Synthesis of Thyrotropin-ReleasingHormone (TRH) General procedure: Boc-L-His-OH (1.2 mmol) (1) was dissolved in about10-12 mL of dry DMF followed by addition of 1.8 mmol(1.5 equiv.) of HONB and DIC each and the reactionmixture was stirred for 15 minutes (Scheme 1).This was followed by addition of 1.8 mmol (1.5 equiv.) of L-Prolinamide and reaction mixture was stirred for36 h at room temperature to afford Boc-L-His-L-Pro-NH2(2), which was purified using column chromatography.Further, the Boc group was deprotected using 10 mL of 7N-methanolic HCl and the resulting substrate wasneutralized using 3 equiv. of DIPEA and then coupled withL-Pyro-Glu-OH in the presence of HONB (1.5 equiv.) andDIC (1.5 equiv.) under constant stirring for 36 hours atroom temperature to obtain L-pGlu-L-His-L-Pro-NH2 (4).The final product 4 was purified using column chromatographyand all the synthesized compounds were analyzedand characterized at each stage using 1H-NMR and massspectrometry.

Reference： [1]Current Patent Assignee: GEORGETOWN UNIVERSITY - US7202279, 2007, B1 Location in patent: Page/Page column 48
[2]Kaur, Sarabjit; Bhararia, Avani; Sharma, Krishna K.; Mittal, Sherry; Jain, Rahul; Wangoo, Nishima; Sharma, Rohit K. [Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 5, p. 5324 - 5332]

13
[ 13139-16-7 ]
[ 7536-55-2 ]
[ 2488-17-7 ]
[ 13726-85-7 ]
[ 13734-34-4 ]
[ 13836-37-8 ]
[ 54613-99-9 ]
[ 13139-14-5 ]
[ 17791-52-5 ]
HFRWRQIKIWFQNRRM[O]KWKK-NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: All protected amino acids were coupled in CH2Cl2 (5 ml) using DCC (2.5 equiv.) and HOBt (2.5 equiv.) until completion (3 h) judged by Kaiser [15] ninhydrin test. After coupling of the appropriate amino acid, Boc deprotection was effected by use of TFA/CH2Cl2 (1:1, 5 ml)) for 5 min first then repeated for 25 min. Following neutralization with 10% TEA/CH2Cl2 three times (5-5 ml of each), the synthetic cycle was repeated to assemble the resin-bond protected peptide. The peptides were cleaved from the resin with simultaneous side chain deprotection by acidolysis with anhydrous hydrogen fluoride (5 ml) containing 2% anisole, 8% dimethyl sulfide and indole at 5 C for 45 min. The crude peptides were dissolved in aqueous acetic acid and lyophilized.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 370 - 377

14
[ 17791-52-5 ]
[ 22888-59-1 ]
[ 1184963-21-0 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 671 - 676

15
[ 17791-52-5 ]
[ 22888-59-1 ]
[ 1185192-61-3 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 671 - 676

16
[ 16652-76-9 ]
[ 17791-52-5 ]
N-Boc-His-Val-OBn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃;	General procedure: EDC hydrochloride (1.1 equiv) and HOBt (1.2 equiv) were added to the solution of N-BocXaaOH (Xaa=Gln, Glu(OMe), Lys(N-Cbz), 1.0 equiv), TsOH salt of ValOBn (1.0 equiv), and i-Pr2NEt (1.1 equiv) in DMF at 0C. The mixture was stirred for 2h at 0C and overnight at room temperature, and concentrated in vacuo. The residue was dissolved in CH2Cl2, and washed with 4% NaHCO3, 1M HCl, and water. The organic layer was dried over Na2SO4 and concentrated in vacuo giving a residue that was subjected to silica gel column chromatography using hexane/AcOEt or CH2Cl2/MeOH as eluents to give the desired protected dipeptide N-BocXaaValOBn (65-87%).

Reference： [1]Tetrahedron,2015,vol. 71,p. 1117 - 1123

17
[ 24424-99-5 ]
[ 1007-42-7 ]
[ 17791-52-5 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 41951 - 41961

18
[ 17791-52-5 ]
[ 24305-27-9 ]

Reference： [1]Journal of Nanoscience and Nanotechnology,2016,vol. 16,p. 5324 - 5332

19
[ 17791-52-5 ]
[ 103962-10-3 ]
C₂₀H₂₂F₃N₃O₆ [ No CAS ]

Reference： [1]MedChemComm,2016,vol. 7,p. 1925 - 1931

20
[ 74-79-3 ]
[ 17791-52-5 ]
C₁₇H₂₉N₇O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: N-(tert-butoxycarbonyl)-L-histidine With 1,1'-carbonyldiimidazole In dichloromethane Stage #2: L-arginine With dmap In N,N-dimethyl-formamide at 80℃;	Method B (3b, 3d and 3h) General procedure: To a solution of the correspondent carboxylic acid (1.2 equiv.) in dry DCM (volume to make a0.5 M solution of substrate) CDI (1.5 equiv.) was added, and the reaction was stirred until completeconsumption of the starting material (TLC, DCM/MeOH 19:1). Then, the reaction mixture wasconcentrated under vacuum and to the attained residue a solution of the arginine derivative (1equiv.) in DMF (volume to make a 0.5 M solution of substrate) and DMAP (0.1 equiv.) were addedand the reaction was stirred at 80 °C until complete consumption of the starting material (TLC,DCM/MeOH/H2O 13:7:1). After the consumption of the starting material, the solvent was removedunder reduced pressured and the reaction mixture was purified by RP-18 column chromatography.The collected fractions were analyzed by UV-vis and combined according to the obtainedUV-spectra.

Reference： [1]Rippel, Rafael; Pinheiro, Luís; Lopes, Mónica; Lourenço, Ana; Ferreira, Luísa M.; Branco, Paula S. [Molecules, 2020, vol. 25, # 4]

21
[ 28122-14-7 ]
[ 17791-52-5 ]
C₁₉H₂₄FN₃O₆S [ No CAS ]

Reference： [1]Organic Letters,2021,vol. 23,p. 530 - 534

22
[ 1158264-69-7 ]
[ 17791-52-5 ]
tert-butyl ((S)-1-(((2-((S)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)carbamate [ No CAS ]
tert-butyl ((S)-1-(((2-((R)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 41% 2: 21%	With N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate In N,N-dimethyl-formamide at 20℃; for 18h;	24 Step 1. 3-[5-(aminomethyl)-1-oxo-2,3-dihydro-1H-isoindol-2-yl]piperidine-2,6-dione hydrochloride (60.0 mg, 0.194 mmol) and Boc-His-OH (59.3 mg, 0.232 mmol) were dissolved in DMF (6 mL). DIPEA (0.074 mL, 0.426 mmol) was added followed by HATU (88.4 mg, 0.232 mmol) and the resulting solution was stirred at RT for 18h. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give 41 mg of tert-butyl ((S)-1-(((2-((S)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5- yl)methyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)carbamate (41% yield) of and 21.0 mg of tert- butyl ((S)-1-(((2-((R)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)amino)-3-(1H-imidazol-4-yl)-1- oxopropan-2-yl)carbamate (21% yield). tert-butyl ((S)-1-(((2-((S)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)amino)-3-(1H-imidazol-4- yl)-1-oxopropan-2-yl)carbamate LCMS: (ESI+) m/z 511.6 [M+H]+ 1H NMR (500 MHz, DMSO) δ 13.99 (s, 2H), 10.98 (s, 1H), 8.92 (s, 1H), 8.53 (t, J = 5.8 Hz, 1H), 7.66 (d, J = 7.8 Hz, 1H), 7.42 (s, 1H), 7.32 (d, J = 8.3 Hz, 2H), 7.22 (d, J = 8.4 Hz, 1H), 5.12 (dd, J = 13.3, 5.1 Hz, 1H), 4.47 - 4.24 (m, 5H), 3.11 (dd, J = 15.0, 5.8 Hz, 1H), 2.98 - 2.86 (m, 2H), 2.67 - 2.56 (m, 1H), 2.46 - 2.34 (m, 1H), 2.05 - 1.97 (m, 1H), 1.36 (s, 9H). tert-butyl ((S)-1-(((2-((R)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)amino)-3-(1H-imidazol-4- yl)-1-oxopropan-2-yl)carbamate LCMS: (ESI+) m/z 511.6 [M+H]+ 1H NMR (500 MHz, DMSO) δ 11.86 (s, 1H), 10.98 (s, 1H), 8.40 (t, J = 5.7 Hz, 1H), 7.69 - 7.49 (m, 2H), 7.24 (s, 2H), 7.06 (d, J = 7.8 Hz, 1H), 6.81 (s, 1H), 5.11 (dd, J = 13.3, 5.1 Hz, 1H), 4.45 - 4.17 (m, 5H), 2.99 - 2.78 (m, 3H), 2.62 (t, J = 12.2 Hz, 1H), 2.48 - 2.35 (m, 1H), 2.01 (ddd, J = 10.4, 5.2, 2.7 Hz, 1H), 1.39 (s, 9H).
1: 41% 2: 21%	With N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate In N,N-dimethyl-formamide at 20℃; for 18h;	24 Step 1. 3-[5-(aminomethyl)-1-oxo-2,3-dihydro-1H-isoindol-2-yl]piperidine-2,6-dione hydrochloride (60.0 mg, 0.194 mmol) and Boc-His-OH (59.3 mg, 0.232 mmol) were dissolved in DMF (6 mL). DIPEA (0.074 mL, 0.426 mmol) was added followed by HATU (88.4 mg, 0.232 mmol) and the resulting solution was stirred at RT for 18h. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give 41 mg of tert-butyl ((S)-1-(((2-((S)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5- yl)methyl)amino)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)carbamate (41% yield) of and 21.0 mg of tert- butyl ((S)-1-(((2-((R)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)amino)-3-(1H-imidazol-4-yl)-1- oxopropan-2-yl)carbamate (21% yield). tert-butyl ((S)-1-(((2-((S)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)amino)-3-(1H-imidazol-4- yl)-1-oxopropan-2-yl)carbamate LCMS: (ESI+) m/z 511.6 [M+H]+ 1H NMR (500 MHz, DMSO) δ 13.99 (s, 2H), 10.98 (s, 1H), 8.92 (s, 1H), 8.53 (t, J = 5.8 Hz, 1H), 7.66 (d, J = 7.8 Hz, 1H), 7.42 (s, 1H), 7.32 (d, J = 8.3 Hz, 2H), 7.22 (d, J = 8.4 Hz, 1H), 5.12 (dd, J = 13.3, 5.1 Hz, 1H), 4.47 - 4.24 (m, 5H), 3.11 (dd, J = 15.0, 5.8 Hz, 1H), 2.98 - 2.86 (m, 2H), 2.67 - 2.56 (m, 1H), 2.46 - 2.34 (m, 1H), 2.05 - 1.97 (m, 1H), 1.36 (s, 9H). tert-butyl ((S)-1-(((2-((R)-2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)amino)-3-(1H-imidazol-4- yl)-1-oxopropan-2-yl)carbamate LCMS: (ESI+) m/z 511.6 [M+H]+ 1H NMR (500 MHz, DMSO) δ 11.86 (s, 1H), 10.98 (s, 1H), 8.40 (t, J = 5.7 Hz, 1H), 7.69 - 7.49 (m, 2H), 7.24 (s, 2H), 7.06 (d, J = 7.8 Hz, 1H), 6.81 (s, 1H), 5.11 (dd, J = 13.3, 5.1 Hz, 1H), 4.45 - 4.17 (m, 5H), 2.99 - 2.78 (m, 3H), 2.62 (t, J = 12.2 Hz, 1H), 2.48 - 2.35 (m, 1H), 2.01 (ddd, J = 10.4, 5.2, 2.7 Hz, 1H), 1.39 (s, 9H).

Reference： [1]Current Patent Assignee: CAPTOR THERAPEUTICS - WO2022/29138, 2022, A1 Location in patent: Page/Page column 65-67
[2]Current Patent Assignee: CAPTOR THERAPEUTICS - WO2022/29138, 2022, A1 Location in patent: Page/Page column 65-67

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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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[ 17791-52-5 ] Synthesis Path-Upstream 1~16

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Amino Acid Derivatives

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