(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester

Base Information

Chemical Name:(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester
CAS No.:1001096-02-1
Molecular Formula:C₂₂H₂₄F₂NO₄P
Molecular Weight:435.407
Hs Code.:

Synonyms:(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester

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Chemical Property of (1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester

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Technology Process of (1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester

There total 4 articles about (1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

: 1001095-46-0
C₁₅H₂₀NO₄P

: 85118-00-9
2,6-Difluorobenzyl bromide

: 1001096-02-1
(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester

Guidance literature:: C₁₅H₂₀NO₄P; With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

2,6-Difluorobenzyl bromide; In dichloromethane; at 40 ℃; for 12.05h; optical yield given as %de; Inert atmosphere;
DOI:10.1016/j.tetlet.2012.02.111

Reference yield:

: 877068-79-6
(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-phosphonic acid monoethyl ester

: 1001096-02-1
(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 2 h / 0 °C

2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -78 - 20 °C

2.2: Cooling with ice

3.1: chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.2: 12.05 h / 40 °C / Inert atmosphere

With chloro-trimethyl-silane; oxalyl dichloride; lithium tri-t-butoxyaluminum hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tetlet.2012.02.111

Reference yield:

: 877068-78-5
C₁₇H₂₄NO₅P

: 1001096-02-1
(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-(2,6-difluoro-benzyl)-phosphinic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine; sodium iodide / 5 h / Reflux

2.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 2 h / 0 °C

3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -78 - 20 °C

3.2: Cooling with ice

4.1: chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.2: 12.05 h / 40 °C / Inert atmosphere

With pyridine; chloro-trimethyl-silane; oxalyl dichloride; lithium tri-t-butoxyaluminum hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; sodium iodide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tetlet.2012.02.111