N-Boc-trans-4-Hydroxy-L-proline methyl ester

Product Name: N-Boc-trans-4-Hydroxy-L-proline methyl ester
CAS No.: 74844-91-0
Chemical Name: N-Boc-trans-4-Hydroxy-L-proline methyl ester
Synonyms: 1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;BOC-HYP-OME;Boc-L-Hyp-OMe;N-BOC-4-HYDROXY-L-PROLINE METHYL ESTER;1-tert-butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;GOSO-001;BoC-Hyp-0me;BOC-L-Hyp Methyl ester;BOC-HYDROXYPROLINE-OME;N-Boc-trans-4-hydroxy-L
CBNumber: CB2207339
Molecular Formula: C11H19NO5
Formula Weight: 245.27
MOL File: 74844-91-0.mol

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N-Boc-trans-4-Hydroxy-L-proline methyl ester Property

Melting point:: 92-96 °C (lit.)
alpha: -65 º (c=1 CHCl3)
Boiling point:: 132°C/0.05mmHg(lit.)
Density: 1.216±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Soluble in chloroform, dichloromethane and ethyl acetate.
form: Crystalline Powder
pka: 14.27±0.40(Predicted)
color: White to light beige
optical activity: [α]20/D -65°, c = 1% in chloroform
InChI: InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1
InChIKey: MZMNEDXVUJLQAF-SFYZADRCSA-N
SMILES: N1(C(OC(C)(C)C)=O)C[C@H](O)C[C@H]1C(OC)=O
LogP: 0.813 at 25℃
CAS DataBase Reference: 74844-91-0(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38
Safety Statements: 24/25-36-26
WGK Germany: 3
HazardClass: IRRITANT
HS Code: 29339900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 639737
Product name: N-Boc-trans-4-hydroxy-L-proline methyl ester
Purity: 97%
Packaging: 5g
Price: $21.36
Updated: 2025/07/31

TCI Chemical

Product number: B3843
Product name: N-(tert-Butoxycarbonyl)-trans-4-hydroxy-L-proline Methyl Ester
Purity: >95.0%(GC)
Packaging: 1g
Price: $30
Updated: 2025/07/31

TCI Chemical

Product number: B3843
Product name: N-(tert-Butoxycarbonyl)-trans-4-hydroxy-L-proline Methyl Ester
Purity: >95.0%(GC)
Packaging: 5g
Price: $87
Updated: 2025/07/31

TRC

Product number: H656560
Product name: (2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylicAcid1-tert-ButylEster2-MethylEster
Packaging: 250g
Price: $485
Updated: 2021/12/16

AK Scientific

Product number: J91745
Product name: Boc-trans-4-Hydroxy-L-prolinemethylester
Packaging: 5g
Price: $10
Updated: 2021/12/16

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N-Boc-trans-4-Hydroxy-L-proline methyl ester Chemical Properties,Usage,Production

Chemical Properties

Clear Colourless Oil

Uses

A potential iNOS inhibitor.

Uses

It is used in the synthesis of For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold.

Uses

(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester roline scaffold.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

24424-99-5

40216-83-9

74844-91-0

The general procedure for the synthesis of N-Boc-trans-4-hydroxy-L-proline methyl ester from di-tert-butyl dicarbonate and trans-4-hydroxy-L-proline methyl ester hydrochloride was as follows: the trans-4-hydroxy-L-proline methyl ester hydrochloride (14.5 g, 0.1 mol) obtained in step I was suspended in CH2Cl2 (400 mL), cooled to 0 °C, and with stirring, sequentially Et3N (28 mL, 0.2 mol), DMAP (0.61 g, 5 mmol) and Boc anhydride (27.5 mL, 0.12 mol) were added. The reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure, ether was added to the residual solid, the solid was collected by filtration and washed well with ether. The filtrates were combined and concentrated under reduced pressure. The residue was dissolved in CH2Cl2, washed with saturated aqueous NaHCO3 and saturated aqueous NaCl in turn, and the organic phase was dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give a light yellow oil, which was solidified by high vacuum treatment. The resulting solid was ground several times with hexane and dried in high vacuum to obtain 1-tert-butyl-2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate as a white solid (24.5 g, 100% yield). The product characterization data were as follows:(M+1) 245; 1H NMR (CDCl3, 300MHz) δ 4.54-4.37 (m, 2H), 3.75 (s, 3H), 3.70-3.40 (m, 2H), 2.48-2.21 (m, 2H), 2.13-2.0 (m, 1H), 1.46 (s, 3H), 1.41 (s, 6H).

IC 50

Non-cleavable Linker

References

[1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5699 - 5702
[2] Patent: WO2007/113634, 2007, A1. Location in patent: Page/Page column 60-61
[3] Tetrahedron Asymmetry, 2009, vol. 20, # 12, p. 1433 - 1436
[4] Journal of Chemical Research, 2009, # 11, p. 668 - 670
[5] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3847 - 3849

N-Boc-trans-4-Hydroxy-L-proline methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

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N-Boc-trans-4-Hydroxy-L-proline methyl ester Suppliers

Americas 1 Belgium 5 Canada 4 China 377 Europe 4 Germany 6 India 15 Japan 4 Switzerland 3 United Kingdom 10 United States 49 Global 478

Sci General Material & Chemical Ltd

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Jiangsu Jitai Peptide Technology Co., Ltd.

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ITIC MEDCHEM(SUZHOU) CO.,LTD.

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View Lastest Price from N-Boc-trans-4-Hydroxy-L-proline methyl ester manufacturers

Hebei Chuanghai Biotechnology Co., Ltd

Product: N-Boc-trans-4-Hydroxy-L-proline methyl ester 74844-91-0
Price: US $30.00-10.00/KG
Min. Order: 50KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-10-24

Hebei Yanxi Chemical Co., Ltd.

Product: N-Boc-trans-4-Hydroxy-L-proline methyl ester 74844-91-0
Price: US $20.00-1.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 20 tons
Release date: 2023-11-29

Nanjing Fred Technology Co., Ltd

Product: N-Boc-trans-4-Hydroxy-L-proline methyl ester 74844-91-0
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1 ton
Release date: 2024-01-02

74844-91-0, N-Boc-trans-4-Hydroxy-L-proline methyl esterRelated Search:

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(2S,4R)-1-BOC-4-hydroxy pyrrolidine-2-carboxylic acid methyl ester

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N-Boc-trans-4-hydroxy-L-proline methyl ester 97%

N-BOC-L-Hydroxyproline methyl ester

BOC-L-Hyp Methyl ester

Boc-L-Hyp-OMe

trans-N-Boc-4-hydroxy-L-proline Methyl Ester

N-(tert-Butoxycarbonyl)-trans-4-hydroxy-L-proline methyl ester

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

O1-tert-Butyl O2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

(2S,4R)-N-Boc-trans-4-hydroxy-L-proline methyl ester

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BOC-HYP-OME

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trans-N-Boc-4-hydroxy-L-proline Methyl Ester,99%e.e.

1-O-tert-butyl 2-O-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

(Tert-Butoxy)Carbonyl Hyp-OMe

GOSO-001

(2S,4R)-N-Boc-4-hydroxyproline methyl ester

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Tert butoxycarbonyl-l-hydroxyproline methyl ester