(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride

Product Name: (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride
CAS No.: 1448189-80-7
Chemical Name: (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride
Synonyms: VHL Ligand 1;ULM-1;ULM-1(MDK7526HCL);VHL Ligand 1 HCl salt;141003;CS-2718;ULM-1 HCl;UBI-10003;MDK7526 HCl;MDK-7526;ULM-1
CBNumber: CB63156669
Molecular Formula: C22H31ClN4O3S
Formula Weight: 467.03
MOL File: 1448189-80-7.mol

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(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride Property

storage temp.: 2-8°C
solubility: DMF: 20 mg/ml; DMSO: 20 mg/ml; Ethanol: 20 mg/ml; PBS (pH 7.2): 10 mg/ml
form: A crystalline solid
color: White to yellow
Appearance: yellow-brown powder
InChIKey: JYRTWGCWUBURGU-XIMRXPCLNA-N
SMILES: C([C@@H]1C[C@@H](O)CN1C(=O)[C@@H](N)C(C)(C)C)(=O)NCC1C=CC(C2=C(N=CS2)C)=CC=1.Cl |&1:1,3,9,r|

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Safety

HS Code: 2934100090

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 901490
Product name: (S,R,S)-AHPC hydrochloride
Purity: ≥97%
Packaging: 100MG
Price: $545
Updated: 2025/07/31

Cayman Chemical

Product number: 21591
Product name: VHL Ligand 1 (hydrochloride)
Purity: ≥95%
Packaging: 10mg
Price: $72
Updated: 2024/03/01

Cayman Chemical

Product number: 21591
Product name: VHL Ligand 1 (hydrochloride)
Purity: ≥95%
Packaging: 25mg
Price: $151
Updated: 2024/03/01

Cayman Chemical

Product number: 21591
Product name: VHL Ligand 1 (hydrochloride)
Purity: ≥95%
Packaging: 50mg
Price: $249
Updated: 2024/03/01

Cayman Chemical

Product number: 21591
Product name: VHL Ligand 1 (hydrochloride)
Purity: ≥95%
Packaging: 100mg
Price: $353
Updated: 2024/03/01

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(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride Chemical Properties,Usage,Production

Description

VHL ligand 1 is a building block in the synthesis of proteolysis-targeting chimera technologies (PROTACs). It is the von Hippel-Lindau (VHL) E3 ligase binding portion of some VHL-based PROTACs, including BET PROTAC MZ1 (Item No. 21622).

Uses

(2S,4R)-1-((S)-2-Amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide Hydrochloride acts as a reagent in the synthesis of PROTAC compounds that mediated the degration of oncogenic c-ABL and BCR-ABL.

Uses

(S,R,S)-AHPC (HCl salt) is a ligand used in the recruitment of the von Hippel-Lindau (VHL) protein for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This (S,R,S) conformation is the active variant, and (S,S,S) is the inactive derivative (cat#901487) used as a negative control.

reaction suitability

reagent type: ligand

Synthesis

1448189-98-7

1448189-80-7

Step 4: Synthesis of (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride (ULM-1) To a stirred solution of tert-butyl N-[(2S)-1-[(2S,4R)-4-hydroxy-2-({[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}carbamoyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate (12 g, 22.61 mmol) in dioxane (20 mL) at room temperature was added to a dioxane solution of hydrogen chloride (4N, 80 mL). The reaction mixture was stirred at room temperature for 2 h. LC-MS monitoring showed formation of the target product. The precipitated solid was collected by filtration to give ULM-1 in 48% yield as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 9.84-9.82 (s, 1H), 7.58-7.54 (m, 4H), 4.71-4.41 (m, 4H), 4.13-4.08 (m, 1H), 3.86-3.71 (m, 2H), 3.36 (s, 1H), 2.60-2.58 (s, 3H), 2.35-2.07 (m, 2H), 1.19-1.12 (m, 9H). LC-MS (ES+): m/z 431.11 [MH+], tR = 0.73 min (run time 2.0 min).

IC 50

VHL

References

[1] Patent: WO2016/118666, 2016, A1. Location in patent: Paragraph 0398; 0399; 0411; 0412
[2] Patent: US2017/8904, 2017, A1. Location in patent: Paragraph 0376; 0382
[3] Patent: US2017/281784, 2017, A1. Location in patent: Paragraph 0191; 0197
[4] Patent: US2018/125821, 2018, A1
[5] Patent: WO2014/108452, 2014, A1. Location in patent: Page/Page column 50

(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride Suppliers

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Zhengzhou Anbu Chem Co.,Ltd

Product: (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride 1448189-80-7
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1000KGS
Release date: 2023-11-06

Xian confluore Biological Technology Co., Ltd.

Product: (S,R,S)-AHPC hydrochloride 1448189-80-7
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Purity: >95.00%
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Release date: 2024-04-01

PNP Biotech Co. Ltd

Product: MDK-7526 HCl 1448189-80-7
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Purity: 98%-99%
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Release date: 2022-09-16

1448189-80-7, (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochlorideRelated Search:

Cereblon Ligand 1 4-Hydroxy ThalidoMide Protein degrader 1 (TFA) 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione L-Prolinamide, 3-methyl-L-valyl-4-hydroxy-N-[(1S)-1-[4-(4-methyl-5-thiazolyl)phenyl]ethyl]-, (4R)-

(S,R,S)-AHPC hydrochloride

MDK-7526;ULM-1

(4R)-3-Methyl-L-valyl-4-hydroxy-N-[[4-(4-methyl-5-thiazolyl)phenyl]methyl]-L-prolinamide hydrochloride

Protein degrader 1

141003

(2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide hydrochloride

CS-2718

Degradation Inducing Moiety A

PROTEIN DEGRADER 1 HYDROCHLORIDE; MDK7526 HCL; MDK7526; MDK-7526; MDK 7526; VHL LIGAND 1; ULM-1; VH032 DESACETYL HYDROCHLORIDE; VH032 AMINE HCL; DEGRADATION INDUCING MOIETY A;

VH032 amine HCl

VH032 desacetyl Hydrochloride

VHL Ligand 1

(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride

Protein degrader 1 (hydrochloride)

ULM-1

MDK7526 HCl

(2S,4R)-1-((S)-2-Amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine

ULM-1(MDK7526HCL)

VHL Ligand 1 (hydrochloride)

PROTAC-VHL-Ligand 1

ULM-1 HCl

PROTAC-VHL-ligand hydrochloride

VHL Ligand 1 HCl salt

(S,R,S)-AHPC hydrochloride >=97%

MDK7526(Protein degrader 1)

(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride ISO 9001：2015 REACH

VH032-NH2 hydrochloride

VHL ligand 1 hydrochlorid

Protein degrader 1 HCl)

ULM-1HCl (MDK7526 HCl

UBI-10003

(S,R,S)-AHPC (VH032-NH2) hydrochloride

L-Prolinamide, 3-methyl-L-valyl-4-hydroxy-N-[[4-(4-methyl-5-thiazolyl)phenyl]methyl]-, (4R)-, HCl

(2S,4R)-1-((S)-2-Amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride, E3 Ligase ligand, Ligand for PROTAC? research, VH032

(S,R,S)-AHPC (monohydrochloride)

(S,R,S)-AHPC hydrochloride

(4R)-3-Methyl-L-valyl-4-hydroxy-N-[[4-(4-methyl-5-thiazolyl)phenyl]methyl]-L-prolinamide hydrochloride (1:1)

1448189-80-7