130369-36-7

Basic information

• Product Name: BENZYL 3-OXOCYCLOBUTYLCARBAMATE
• Synonyms: BENZYL 3-OXOCYCLOBUTYLCARBAMATE;(3-Oxo-cyclobutyl)-carbamic acid benzyl ester;N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanone;(3-Oxocyclobutyl)carbamic acid phenylmethyl ester;benzyl N-(3-oxocyclobutyl)carbamate;Carbamic acid, N-(3-oxocyclobutyl)-, phenylmethyl ester;3-Z-amino-cyclobutanone, 98%
• CAS NO: 130369-36-7
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.239
• EINECS: 1533716-785-6
• Mol File: 130369-36-7.mol

Chemical Properties

• Boiling Point: 403.3 °C at 760 mmHg
• Flash Point: 197.7 °C
• Appearance: White crystalline powder
• Density: 1.22
• Vapor Pressure: 1.03E-06mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: 2-8°C
• PKA: 11.39±0.20(Predicted)
• CAS DataBase Reference: BENZYL 3-OXOCYCLOBUTYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 3-OXOCYCLOBUTYLCARBAMATE(130369-36-7)
• EPA Substance Registry System: BENZYL 3-OXOCYCLOBUTYLCARBAMATE(130369-36-7)

Safety Data

• Hazardous Substances Data: 130369-36-7(Hazardous Substances Data)

Usage

Uses

Benzyl 3-Oxocyclobutylcarbamate is used in process for preparation of abrocitinib.

InChI:InChI=1/C12H13NO3/c14-11-6-10(7-11)13-12(15)16-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,15)

Upstream product

• 96-50-4 2-thiazolylamine 
• 75-77-4 chloro-trimethyl-silane 
• 23761-23-1 3-oxocyclobutanecarboxylic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 939399-53-8 benzyl (3,3-difluorocyclobutyl)carbamate 
• 305859-68-1 (R,S)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone 
• 87219-29-2 benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate 
• 118399-28-3 (R)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone 
• 1201825-73-1 benzyl [cis-3-(methylamino)cyclobutyl]carbamate 
• 1201825-73-1 benzyl [cis-3-(methylamino)cyclobutyl]carbamate 
• 1201825-73-1 benzyl [trans-3-(methylamino)cyclobutyl]carbamate 
• 1609978-79-1 trans-3-{[(benzyloxy)carbonyl]amino}cyclobutyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate 

Relevant articles and documents

Development of a Nitrene-Type Rearrangement for the Commercial Route of the JAK1 Inhibitor Abrocitinib

The development of a commercial route toward the JAK1 inhibitor abrocitinib is described. The application of a late-stage Lossen rearrangement provided the desired cis-diaminocyclobutane, which was subsequently sulfonylated using a novel water-tolerable triazole sulfonylating reagent to provide the active pharmaceutical ingredient.

Coupling biocatalysis with high-energy flow reactions for the synthesis of carbamates and β-amino acid derivatives

A continuous flow process is presented that couples a Curtius rearrangement step with a biocatalytic impurity tagging strategy to produce a series of valuable Cbz-carbamate products. Immobilized CALB was exploited as a robust hydrolase to transform residual benzyl alcohol into easily separable benzyl butyrate. The resulting telescoped flow process was effectively applied across a series of acid substrates rendering the desired carbamate structures in high yield and purity. The derivatization of these products via complementary flow-based Michael addition reactions furthermore demonstrated the creation of β-amino acid species. This strategy thus highlights the applicability of this work towards the creation of important chemical building blocks for the pharmaceutical and speciality chemical industries.

PROCESS FOR PREPARATION OF ABROCITINIB

The present invention relates to crystalline abrocitinib characterized by X-ray powder diffraction (XRPD) spectrum having peak reflections at about 12.9, 14.7, 19.4, 23.2 and 25.2 ±0.2 degrees 2 theta, and process for its preparation. The present invention relates to amorphous solid dispersion comprising abrocitinib or salt thereof together with at least one pharmaceutically acceptable carrier and process for its preparation.

COMPOUNDS AS CRTH2 ANTAGONIST AND USES THEREOF

The compounds of Formula (I) which can be used as CRTH2 receptor antagonists are provided. The compounds of Formula (I) can be used in the treatment and prevention of asthma, allergic rhinitis and atopic dermatitis, as well as other diseases mediated by prostaglandin D2 (PGD2) at the CRTH2 receptor.

PRODRUG BIPYRIDYLAMINOPYRIDINES AS SYK INHIBITORS

The present invention provides compounds of Formula (I), which are prodrugs of trans-4-[(1R)-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylic acid, a potent inhibitor of Syk. The compounds are useful in the treatment and prevention of diseases mediated by the enzyme, such as asthma, COPD, rheumatoid arthritis and cancer.

SUBSTITUTED PURINE AND 7 - DEAZAPURINE COMPOUNDS AS MODULATORS OF EPIGENETIC ENZYMES

The present invention relates to substituted purine and 7-deazapurine compounds. The present invention also relates to pharmaceutical compositions containing these compounds and methods of treating disorders in which DOTl -mediated protein methylation plays a part, such as cancer and neurological disorders, by administering these compounds and pharmaceutical compositions to subjects in need thereof.

THERAPEUTICALLY ACTIVE COMPOSITIONS AND THEIR METHOD OF USE

Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1 comprising administering to a subject in need thereof a compound described here.

Thiazole derivatives

The invention provides compounds of formula 1 wherein R1, R3, and R4 are as defined, and their pharmaceutically acceptable salts. Compounds of formula 1 are indicated to have activity inhibiting cdk5, cdk2, and GSK-3. Pharmaceutical compositions and methods comprising compounds of formula 1 for treating diseases and conditions comprising abnormal cell growth, such as cancer, and neurodegenerative diseases and conditions and those affected by dopamine neurotransmission are described. Also described are pharmaceutical compositions and methods comprising compounds of formula 1 for treating male fertility and sperm motility; diabetes mellitus; impaired glucose tolerance; metabolic syndrome or syndrome X; polycystic ovary syndrome; adipogenesis and obesity; myogenesis and frailty, for example age-related decline in physical performance; acute sarcopenia, for example muscle atrophy and/or cachexia associated with burns, bed rest, limb immobilization, or major thoracic, abdominal, and/or orthopedic surgery; sepsis; hair loss, hair thinning, and balding; and immunodeficiency.

Thiazole derivatives and their use as cdk inhibitors

The invention provides compounds of formula 1 wherein R1, R3, and R4 are as defined, and their pharmaceutically acceptable salts. Compounds of formula 1 are indicated to have activity inhibiting cdk5, cdk2, and GSK-3. Pharmaceutical compositions and methods comprising compounds of formula 1 for treating diseases and conditions comprising abnormal cell growth, such as cancer, and neurodegenerative diseases and conditions and those affected by dopamine neurotransmission are described. Also described are pharmaceutical compositions and methods comprising compounds of formula 1 for treating male fertility and sperm motility; diabetes mellitus; impaired glucose tolerance; metabolic syndrome or syndrome X; polycystic ovary syndrome; adipogenesis and obesity; myogenesis and frailty, for example age-related decline in physical performance; acute sarcopenia, for example muscle atrophy and/or cachexia associated with burns, bed rest, limb immobilization, or major thoracic, abdominal, and/or orthopedic surgery; sepsis; hair loss, hair thinning, and balding; and immunodeficiency.