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Structure of VH032 thiol
CAS No.: 2098836-54-3

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Synonyms: VHL ligand 6

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Quality Control of [ 2098836-54-3 ] Purity: 95% SDS Specification

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Product Details of [ 2098836-54-3 ]

CAS No. :	2098836-54-3
Formula :	C₂₃H₃₀N₄O₄S₂
M.W :	490.64
SMILES Code :	O=C(NCC1=CC=C(C2=C(C)N=CS2)C=C1)[C@H]3N(C([C@H](C(C)(S)C)NC(C)=O)=O)C[C@H](O)C3
Synonyms :	VHL ligand 6
English Name :	(2S,4R)-1-((R)-2-Acetamido-3-mercapto-3-methylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

Safety of [ 2098836-54-3 ]

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Application In Synthesis of [ 2098836-54-3 ]

* 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 [ 2098836-54-3 ]

[ 2098836-54-3 ] Synthesis Path-Downstream 1~10

Yield	Reaction Conditions	Operation in experiment
79%	With triisopropylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 2h;	(2R,3R,4S)-1 -((R)-2-acetamido-3-mercapto-3-methylbutanoyl)-3-fluoro-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (23) General procedure: Compound 22 (30 mg, 0.04 mmol) was dissolved in 1.8 mL of DCM. TIPS (0.1 mL) and TFA (0.1 mL) were added, and the yellow mixture was let to react at room temperature for 2 h. HPLC analysis (acidic method) showed complete conversion of the starting material. Volatiles were removed and the crude wasdissolved in MeOH, filtered and purified by preparative HPLC and freeze-dried to give pure deprotected compound as white solid (16 mg, 79% yield). MS analysis: C23H29FN40452 expected 508.2, found 509.2 [M+Hj.‘H NMR (500 MHz, MeOD) : 8.88 (s, 1H), 8.84 (t, J6.0 Hz, OH), 8.14 (d, J=8.9 Hz, 1H), 7.47 - 7.42 (m, 4H), 5.05 - 4.92 (m, 1H), 4.91 (d, J=8.8 Hz, 1H), 4.65 (dd, J=2.5, 21.5 Hz, 1H), 4.57 - 4.37 (m, 3H), 4.29 (dd, J=6.4, 10.3 Hz, 1H), 3.75 - 3.70 (m, 1H), 2.49 (s, 3H), 2.03 (s, 3H), 1.43 (s, 3H), 1.40 (s, 3H).19FNMR: -199.94 13CNMR: 173.3, 171.5, 170.5, 153.0, 149.2, 140.0, 133.4, 131.8, 130.5, 129.1,95.3, 93.8, 71.1, 70.9, 66.2, 66.0, 59.4, 52.2, 46.8, 43.9, 29.8, 28.8.

2
[ 3077194-16-9 ]
[ 2098836-54-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 25 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0.5 h / 0 °C
	Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h / 25 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0.5 h / 0 °C

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1.
[2]Current Patent Assignee: OERTH BIO - WO2025/49555, 2025, A1.

3
[ 108-24-7 ]
[ CAS Unavailable ]
[ 2098836-54-3 ]

Yield	Reaction Conditions	Operation in experiment
80.65%	With triethylamine In dichloromethane at 0℃; for 0.5h;	C-14.C. Step 3 C. Step 3 To a mixture of (2S, 4R)-1-[(2R)-2-amino-3-methyl-3-sulfanyl-butanoyl]-4-hydroxy-N-[[4-(4-methylthiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide (1.9 g, 3.92 mmol, HCl salt) and Et3N (792.73 mg, 7.83 mmol, 1.09 mL) in CH2Cl2 (20 mL) was added Ac2O (399.89 mg, 3.92 mmol, 367.88 uL, ) at 0 °C. The mixture was stirred at 0 °C for 0.5 hour. The reaction mixture was diluted with water (20 mL). The mixture was extracted with Dichloromethane (25 mL x 3). The combined organic phase was washed with brine (30 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (Dichloromethane/Methanol = 20/1) to afford the desired product (2S,4R)-1-[(2R)-2-acetamido-3-methyl-3-sulfanyl-butanoyl]-4-hydroxy-N-[[4-(4-methylthiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide (1.55 g, 3.16 mmol, 80.65% yield).1H NMR: DMSO-d6, 400 MHz. δ 8.98 (s, 1H), 8.61 (t, J = 6.0 Hz, 1H), 8.13 (d, J = 9.6 Hz, 1H), 7.44 -7.37 (m, 4H), 5.28 - 5.08 (m, 1H), 4.84 (d, J = 9.6 Hz, 1H), 4.48 - 4.33 (m, 3H), 4.29 - 4.24 (m, 1H), 3.91 - 3.83 (m, 1H), 3.67 - 3.61 (m, 1H), 2.44 (s, 3H), 2.14 - 1.93 (m, 2H), 1.91 (s, 3H), 1.38 (s, 3H), 1.28 (s, 3H).

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1 Location in patent: Paragraph 0543.

4
[ 2098836-54-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; tetrabutylammomium bromide / water; ethyl acetate / 16 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; sodium hydrogencarbonate / water; ethyl acetate / 16 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1.
[2]Current Patent Assignee: OERTH BIO - WO2025/49555, 2025, A1.

5
[ 2098836-54-3 ]
[ 3031995-55-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; tetrabutylammomium bromide / water; ethyl acetate / 16 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C / Inert atmosphere 3: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; sodium hydrogencarbonate / water; ethyl acetate / 16 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide; acetonitrile / 16 h / 60 °C / Inert atmosphere

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1.
[2]Current Patent Assignee: OERTH BIO - WO2025/49555, 2025, A1.

6
[ 2098836-54-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; tetrabutylammomium bromide / water; ethyl acetate / 16 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C / Inert atmosphere 3: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere 4: dichloromethane / 1 h / 25 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: tetrabutylammomium bromide; sodium hydrogencarbonate / water; ethyl acetate / 16 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide; acetonitrile / 16 h / 60 °C / Inert atmosphere 4: dichloromethane / 1 h / 25 °C

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1.
[2]Current Patent Assignee: OERTH BIO - WO2025/49555, 2025, A1.

7
[ 2098836-54-3 ]
[ 3031993-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: sodium hydrogencarbonate; tetrabutylammomium bromide / water; ethyl acetate / 16 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C / Inert atmosphere 3: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere 4: dichloromethane / 1 h / 25 °C / Inert atmosphere 5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1 h / 0 - 25 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1: tetrabutylammomium bromide; sodium hydrogencarbonate / water; ethyl acetate / 16 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C 3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide; acetonitrile / 16 h / 60 °C / Inert atmosphere 4: dichloromethane / 1 h / 25 °C 5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1 h / 0 - 25 °C / Inert atmosphere

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1.
[2]Current Patent Assignee: OERTH BIO - WO2025/49555, 2025, A1.

8
[ 2098836-54-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; tetrabutylammomium bromide / ethyl acetate / 15 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; sodium hydrogencarbonate / ethyl acetate / 15 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C / Inert atmosphere

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1.
[2]Current Patent Assignee: OERTH BIO - WO2025/49555, 2025, A1.

9
[ 2098836-54-3 ]
[ 3031993-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; tetrabutylammomium bromide / ethyl acetate / 15 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1 h / 0 - 25 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; sodium hydrogencarbonate / ethyl acetate / 15 h / 0 - 60 °C 2: dichloromethane / 1 h / 25 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1 h / 0 - 25 °C / Inert atmosphere

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1.
[2]Current Patent Assignee: OERTH BIO - WO2025/49555, 2025, A1.

10
[ 2098836-54-3 ]
[ 3031995-57-7 ]
[ 3077194-17-0 ]

Yield	Reaction Conditions	Operation in experiment
46.83%	With tetrabutylammomium bromide; sodium hydrogencarbonate In ethyl acetate at 0 - 60℃; for 15h;	C-15.C. Step 3 C. Step 3 To a mixture of (2S,4R)-1-[(2R)-2-acetamido-3-methyl-3-sulfanyl-butanoyl]-4-hydroxy-N-[[4-(4-methylthiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide (50 mg, 101.91 μmol), tert-butyl N-[2-[4-(2-bromoethyl)phenyl]ethyl]-N-tert-butoxycarbonyl-carbamate (52.38 mg, 122.29 μmol) and TBAB (131.41 mg, 407.63 μmol) in EtOAc (1 mL) was added saturated NaHCO3 solution (302.00 mg, 3.59 mmol, 0.2 mL) at 0 °C. The mixture was stirred at 60 °C for 15 hours. The reaction mixture was diluted with water (5 mL) and extracted with Ethyl acetate (5 mL x 3). The combined organic phase was dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative TLC on silica gel (Dichloromethane/Methanol = 20/1) to afford the desired product tert-butyl N-[2-[4-[2-[(2R)-2-acetamido-3-[(2S,4R)-4-hydroxy-2-[[4-(4-methylthiazol-5-yl)phenyl]methylcarbamoyl]pyrrolidin-1-yl]-1,1-dimethyl-3-oxo-propyl]sulfanylethyl]phenyl]ethyl]-N-tertbutoxycarbonyl-carbamate (40 mg, 47.73 μmol, 46.83% yield) as a yellow oil. LCMS: m/z 838.3 [M+H]+.
	With tetrabutylammomium bromide; sodium hydrogencarbonate In ethyl acetate at 0 - 60℃; for 15h;	C-15.C.3 C. Step 3 To a mixture of (2S,4R)-l-[(2A)-2-acetamido-3-methyl-3-sulfanyl-butanoyl]-4- hydroxy-A-[[4-(4-methylthiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide (50 mg, 101.91 pmol), tert-butyl A-[2-[4-(2-bromoethyl)phenyl]ethyl]-A-tert-butoxycarbonyl-carbamate (52.38 mg, 122.29 pmol) and TBAB (131.41 mg, 407.63 pmol) in EtOAc (1 mL) was added saturated NaHCOs solution (302.00 mg, 3.59 mmol, 0.2 mL) at 0 °C. The mixture was stirred at 60 °C for 15 hours. The reaction mixture was diluted with water (5 mL) and extracted with Ethyl acetate (5 mL x 3). The combined organic phase was dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative TLC on silica gel (Dichloromethane/Methanol = 20/1) to afford the desired product tert-butyl A-[2-[4-[2-[(2R)-2- acetamido-3-[(2S,4R)-4-hydroxy-2-[[4-(4-methylthiazol-5- yl)phenyl]methylcarbamoyl]pyrrolidin-l-yl]-l,l-dimethyl-3-oxo- propyl]sulfanylethyl]phenyl]ethyl]-Ntertbutoxycarbonyl-carbamate (40 mg, 47.73 μmol,46.83% yield) as a yellow oil. LCMS: m/z 838.3 [M+H]+.

References: [1]Current Patent Assignee: OERTH BIO - WO2024/50016, 2024, A1 Location in patent: Paragraph 0551.
[2]Current Patent Assignee: OERTH BIO - WO2025/49555, 2025, A1 Location in patent: Paragraph 0289; 0291.

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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.: 2098836-54-3

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CAS No.: 2098836-54-3

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[ 2098836-54-3 ] Synthesis Path-Downstream 1~10

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