N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER

Product Name: N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER
CAS No.: 81477-91-0
Chemical Name: N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER
Synonyms: DPM-Gly-OBzl;ycine BenzyL;Benzyl N-(diphenylmethylene)glycinate;Diphenylmethylene-Glycine benzyl ester;N-(DIPHENYLMETHYLENE)GLYCINE BENZYL ESTER;Benzyl 2-((diphenylmethylene)amino)acetate;N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL;Benzyl 2-[(diphenylmethylidene)amino]acetate;N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER;Glycine,N-(diphenylmethylene)-, phenylmethyl ester
CBNumber: CB7311864
Molecular Formula: C22H19NO2
Formula Weight: 329.39
MOL File: 81477-91-0.mol

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N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER Property

Melting point:: 86-88 °C
Boiling point:: 446.8±37.0 °C(Predicted)
Density: 1.06±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 2.24±0.50(Predicted)
color: White to Off-White
InChI: InChI=1S/C22H19NO2/c24-21(25-17-18-10-4-1-5-11-18)16-23-22(19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H,16-17H2
InChIKey: KFNIDRLZPBRDNJ-UHFFFAOYSA-N
SMILES: C(OCC1=CC=CC=C1)(=O)C/N=C(/C1=CC=CC=C1)\C1=CC=CC=C1

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Safety

HS Code: 2925199590

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

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

P273Avoid release to the environment.

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

Cayman Chemical

Product number: 10007089
Product name: N-(diphenylmethylene) Glycine benzyl ester
Purity: ≥98%
Packaging: 500mg
Price: $25
Updated: 2024/03/01

Cayman Chemical

Product number: 10007089
Product name: N-(diphenylmethylene) Glycine benzyl ester
Purity: ≥98%
Packaging: 1g
Price: $40
Updated: 2024/03/01

Cayman Chemical

Product number: 10007089
Product name: N-(diphenylmethylene) Glycine benzyl ester
Purity: ≥98%
Packaging: 5g
Price: $113
Updated: 2024/03/01

Cayman Chemical

Product number: 10007089
Product name: N-(diphenylmethylene) Glycine benzyl ester
Purity: ≥98%
Packaging: 10g
Price: $175
Updated: 2024/03/01

TRC

Product number: D492185
Product name: N-(Diphenylmethylene)glycineBenzylEster
Packaging: 25g
Price: $240
Updated: 2021/12/16

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N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER Chemical Properties,Usage,Production

Chemical Properties

White crystals or powder

Uses

N-(Diphenylmethylene)glycine benzyl ester is used as a reagent to synthesize (-)-Lepadiformine, a marine cytotoxic alkaloid that exhibits activity towards lunch carcinoma cell lines. N-(Diphenylmethylene)glycine benzyl ester is also used as a reagent to prepare (+)-Cylindricine C, a marine alkaloid that also shows activity against tumour cell lines.

Synthesis

1013-88-3

2462-31-9

81477-91-0

A 3-necked 5L round bottom flask was equipped with a mechanical stirrer, a J-KEM temperature probe and an N2 inlet adapter connected to a bubbler. Glycine benzyl ester hydrochloride (505.2 g, 2.51 mol, 1.0 eq.) and dichloromethane (3.0 L) were added to the flask. Benzophenone imine (471.1 g, 97% purity, 2.6 mol, 1.00 eq.) was subsequently added to the milky reaction mixture and the reaction was observed to be exothermic (temperature rise of 4.5 °C). The reaction mixture was stirred at 20 °C for 3 h. Detection by TLC (unfolding agent: 50% ethyl acetate/heptane) showed only trace residues of starting material. After addition of benzophenone imine (25.0 g, 0.14 mol), stirring was continued at 20 °C for 15 h. TLC confirmed the completion of the reaction. The reaction mixture was filtered through a short diatomaceous earth pad to remove the ammonium chloride generated and the filter cake was washed with dichloromethane (1.5 L). After combining the filtrates, it was concentrated under reduced pressure to give a white solid, which was further dried under vacuum to obtain the crude product N-diphenylmethylene glycine benzyl ester 878.7 g (106% yield). The product was identified by 1H-NMR (DMSO-d6): δ 7.53-7.25 (m, 13H), 7.12 (dd, 2H), 5.10 (s, 2H) and 4.17 (s, 2H). HPLC analysis showed purity >95%.

References

[1] Patent: US2005/239857, 2005, A1. Location in patent: Page/Page column 82
[2] Patent: WO2007/49121, 2007, A1. Location in patent: Page/Page column 15
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 9, p. 2725 - 2731
[4] Patent: US2005/239857, 2005, A1. Location in patent: Page/Page column 33
[5] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1183 - 1187

N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER manufacturers

Career Henan Chemical Co

Product: N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER 81477-91-0
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%-99.9%
Supply Ability: 200kg
Release date: 2019-09-03

81477-91-0, N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTERRelated Search:

BENZYL N-(DIPHENYLMETHYLENE)-L-SERINATE Ethyl N-(diphenylmethylene)glycinate ([1-PHENYL-METH-(E)-YLIDENE]-AMINO)-ACETIC ACID ETHYL ESTER N-DIPHENYLMETHYLENE-O-(2,3,6,2',3',4',6'-HEPTA-O-ACETYL-BETA-D-LACTOSYL)-L-SERINE, BENZYL ESTER N-(DIPHENYLMETHYLENE)GLYCINE METHYL ESTER N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER

Benzyl 2-[(diphenylmethylidene)amino]acetate

N-(DIPHENYLMETHYLENE)GLYCINE BENZYL ESTER

N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER

Diphenylmethylene-Glycine benzyl ester

DPM-Gly-OBzl DiphenylMethylene-Glycine benzyl ester

DPM-Gly-OBzl

Benzyl 2-((diphenylmethylene)amino)acetate

Glycine,N-(diphenylmethylene)-, phenylmethyl ester

Benzyl N-(diphenylmethylene)glycinate

ycine BenzyL

N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL ESTER USP/EP/BP

N-(DIPHENYLMETHYLENE)-GLYCINE, PHENYLMETHYL

81477-91-0