Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate

Product Name: Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate
CAS No.: 118399-28-3
Chemical Name: Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate
Synonyms: S,β(R)-βR)-Bedaquiline;-Pinene-D2,13C;R)-6-Bromo-αS)-rel-Bedaquiline;-1-naphthalenyl-β-Ethyl-3-methoxy-α-phenyl-3-quinolineethanol;-(Carbobenzoxyamino)-&gamma
CBNumber: CB11092386
Molecular Formula: C12H13NO4
Formula Weight: 235.24
MOL File: 118399-28-3.mol

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Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate Property

Melting point:: 105.0 to 109.0 °C
Boiling point:: 466.1±44.0 °C(Predicted)
Density: 1.27
storage temp.: 2-8°C
solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
form: Solid
pka: 10.87±0.20(Predicted)
color: Off-White
optical activity: Consistent with structure
CAS DataBase Reference: 118399-28-3

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Safety

Hazard Codes: Xi
Safety Statements: 24/25
HazardClass: IRRITANT
HS Code: 29321900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical

Product number: C2678
Product name: (R)-beta-(Carbobenzoxyamino)-gamma-butyrolactone
Purity: >98.0%(HPLC)(N)
Packaging: 1g
Price: $40
Updated: 2025/07/31

TRC

Product number: C176210
Product name: 3(R)-[(Carbobenzyloxy)amino]-γ-butyrolactone
Packaging: 2.5g
Price: $90
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FC19703
Product name: 3(R)-[(Carbobenzyloxy)amino]-gamma-butyrolactone
Packaging: 500mg
Price: $100
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FC19703
Product name: 3(R)-[(Carbobenzyloxy)amino]-gamma-butyrolactone
Packaging: 1g
Price: $150
Updated: 2021/12/16

Chem-Impex

Product number: 41637
Product name: (R)-4-(Benzyloxycarbonylamino)tetrahydrofuran-2-one,98%(HPLC)
Purity: 98%(HPLC)
Packaging: 1G
Price: $50.4
Updated: 2021/12/16

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Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate Chemical Properties,Usage,Production

Chemical Properties

Off-White Solid

Uses

3(R)-[(Carbobenzyloxy)amino]-γ-butyrolactone (cas# 118399-28-3) is a compound useful in organic synthesis.

Synthesis

75443-62-8

118399-28-3

General procedure for the synthesis of benzyl (R)-(5-oxotetrahydrofuran-3-yl)carbamate from benzyl (R)-(2,5-dioxo-tetrahydrofuran-3-yl)carbamate: to a stirred suspension of sodium borohydride (8.38 g, 0.223 mol) in tetrahydrofuran (THF, 290 mL) at 0 °C, a slow dropwise addition of (R)-(2,5-dioxo tetrahydrofuran-3-yl)carbamic acid benzyl ester (46 g, 0.185 mol) solution of THF (290 mL), and the titration process lasted for 3 hours. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 1 hour. Subsequently, the reaction mixture was carefully acidified to pH 2 with 6N hydrochloric acid (HCl) and then concentrated to one-fourth of the original volume under reduced pressure. The concentrated solution was diluted with water and extracted four times with ether. The organic extracts were combined and concentrated under reduced pressure to give a yellow non-homogeneous residue. This residue was dissolved in toluene (200 mL) containing p-toluenesulfonic acid (p-TsOH, 200 mg) and water was removed by azeotropy using a Dean-Stark apparatus. After refluxing the mixture for 5 h, the toluene was removed under reduced pressure to give a viscous residue. Benzyl (R)-(5-oxotetrahydrofuran-3-yl)carbamate (37 g, 85% yield) was obtained as white crystals by grinding with ether.LCMS: 236 [M + 1]+; 1H NMR (DMSO-d6): δ 2.39 (dd, 1H, J1 = 3.6 Hz, J2 = 18.0 Hz), 2.86 (dd, 1H, J1 = 8.1 Hz, J2 = 17.7 Hz), 4.11 (dd, 1H, J1 = 3.6 Hz, J2 = 9.3 Hz), 4.319 (m, 1H), 4.43 (dd, 1H, J1 = 6.0 Hz, J2 = 9.0 Hz), 5.05 (s, 2H), 7.365 (m, 5H), 7.88 (d, 1H, J = 4.5 Hz).

References

[1] Patent: WO2009/36051, 2009, A1. Location in patent: Page/Page column 48
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1040 - 1044
[3] Patent: WO2008/61208, 2008, A2. Location in patent: Page/Page column 31; 32; 34; 35
[4] Patent: US2005/272744, 2005, A1. Location in patent: Page/Page column 20
[5] Patent: US6660769, 2003, B1. Location in patent: Page column 27

Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate Preparation Products And Raw materials

Raw materials

Preparation Products

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Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate Suppliers

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View Lastest Price from Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

Product: (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate 118399-28-3
Price: US $1.10-9.90/kg
Min. Order: 1kg
Purity: 99%min
Supply Ability: 100kg
Release date: 2025-08-18

Career Henan Chemical Co

Product: Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamate 118399-28-3
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 200kg
Release date: 2019-12-31

118399-28-3, Benzyl (R)-5-oxotetrahydrofuran-3-ylcarbamateRelated Search:

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118399-28-3

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