(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
- Product Name
- (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
- CAS No.
- 1428243-26-8
- Chemical Name
- (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
- Synonyms
- (3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate;Upadacitinib intermediate;1-Pyrrolidinecarboxylic acid, 3-(2-bromoacetyl)-4-ethyl-, phenylmethyl ester, (3R,4S)-;Benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate;Upatinib impurity 14;Upatinib intermediate;intermediate of abt594;Upadacitinib Impurity 14;Upadacitinib intermediate5;Upadacitinib Intermediate1
- CBNumber
- CB93311984
- Molecular Formula
- C16H20BrNO3
- Formula Weight
- 354.24
- MOL File
- 1428243-26-8.mol
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester Property
- Boiling point:
- 453.1±45.0 °C(Predicted)
- Density
- 1.361±0.06 g/cm3(Predicted)
- storage temp.
- Storage temp. 2-8°C
- pka
- -2.91±0.60(Predicted)
- Appearance
- White to off-white Solid
- optical activity
- 25.6747°(C=1.0523g/100ml MEOH)
- InChI
- InChI=1S/C16H20BrNO3/c1-2-13-9-18(10-14(13)15(19)8-17)16(20)21-11-12-6-4-3-5-7-12/h3-7,13-14H,2,8-11H2,1H3/t13-,14+/m1/s1
- InChIKey
- QEFUCTKHMXMWRF-KGLIPLIRSA-N
- SMILES
- N1(C(OCC2=CC=CC=C2)=O)C[C@@H](CC)[C@@H](C(CBr)=O)C1
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.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
P362Take off contaminated clothing and wash before reuse.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 6410EA
- Product name
- CID86678506
- Packaging
- 100mg
- Price
- $212
- Updated
- 2021/12/16
- Product number
- CM328300
- Product name
- benzyl(3R,4S)-3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate
- Purity
- 95%+
- Packaging
- 10g
- Price
- $957
- Updated
- 2021/12/16
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester Chemical Properties,Usage,Production
Chemical Properties
Benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylate is extremely sensitive to pH, and the color characteristics of benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylate vary considerably at different pH values, and it exists and exhibits a red color mainly in the form of a molten salt ion when the aqueous pH is below 2, and it exhibits a red color when the pH is in the weak acidic range. pH is in the weakly acidic range, benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylate exists in the form of a colorless methanolic pseudobasic or hemiacetal form, and as the aqueous solution progressively approaches neutrality, benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylate deprotonates to a quinone base, and may also ring-open to the chalcone form.
Uses
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester is a reagent in the preparation of imidazopyrrolopyrazine derivatives and analogs for use as protein kinase modulators.
Preparation
Dimethylsulfoxonium 2-((3R,4S)-1-benzyloxycarbonyl-4-ethylpyrrolidin-3-yl)-2-oxo-ethylide (10.0 g, 28.5 mmol, 1.0 equivalents), THF (100 mL), and 33% HBr in AcOH (8.37 g, 34.1 mmol, 1.2 equivalents) were charged sequentially and heated to 40° C. The reaction mixture was agitated for 5 hours, cooled to 20° C, and then distilled under vacuum to approximately 65 mL. EtOAc (20 mL) and heptane (50 mL) were charged, and the reaction mixture was washed with water (5×50 mL). The organic layer was concentrated under vacuum and chased with EtOAc (2×50 mL) concentrating to dryness each time. N,N-dimethylacetamide (20 mL) was then charged to provide 30.8 g of a 24.0 wt/wt % solution of (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester (yield: 73%).
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester manufacturers
- Product
- (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester 1428243-26-8
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 1000kg
- Release date
- 2025-09-19
- Product
- (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester 1428243-26-8
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1000kg
- Release date
- 2025-06-11
- Product
- Upadacitinib Impurity 14 1428243-26-8
- Price
- US $0.00/mg
- Min. Order
- 10mg
- Purity
- 0.98
- Supply Ability
- 10g
- Release date
- 2024-03-29