(1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid

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Chemical Name:(1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid
CAS No.:603963-06-0
Molecular Formula:C₂₁H₂₈FNO₄
Molecular Weight:377.456
Hs Code.:

Synonyms:(1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid

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Chemical Property of (1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid

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Technology Process of (1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid

There total 9 articles about (1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid 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: 84.0%

: 603962-99-8
[2-fluoro-2-(2-hydroxymethyl-cyclopentylidene)-ethyl]-phenethyl-carbamic acid tert-butyl ester

: 603963-06-0
(1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; for 1.5h;
DOI:10.1021/jm0495982

Reference yield:

: 603962-80-7
(2Z)-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene](fluoro)ethanoic acid

: 603963-06-0
(1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisopropylethylamine; TBTU / CH₂Cl₂ / 0.08 h

1.2: 84 percent / CH₂Cl₂ / 3 h

2.1: POCl₃ / CH₂Cl₂ / 1 h / 0 °C

2.2: LiAlH₄ / diethyl ether / 3 h / 0 °C

3.1: diisopropylethylamine / CH₂Cl₂ / 4 h

4.1: aq. glacial acetic acid / tetrahydrofuran / 8 h / 20 °C

5.1: 84 percent / CrO₃; aq. H₂SO₄ / acetone / 1.5 h

With chromium(VI) oxide; sulfuric acid; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; acetone; 5.1: Jones oxidation;
DOI:10.1021/jm0495982

Reference yield:

: 129600-97-1
2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>cyclopentanone

: 603963-06-0
(1R,S)-(2Z)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / diethyl ether / 0.08 h / -5 °C

1.2: 42 percent / Wadsworth-Horner-Emmons reagent / diethyl ether / 4 h

2.1: 97 percent / aq. KOH / methanol / 8 h / 20 °C

3.1: diisopropylethylamine; TBTU / CH₂Cl₂ / 0.08 h

3.2: 84 percent / CH₂Cl₂ / 3 h

4.1: POCl₃ / CH₂Cl₂ / 1 h / 0 °C

4.2: LiAlH₄ / diethyl ether / 3 h / 0 °C

5.1: diisopropylethylamine / CH₂Cl₂ / 4 h

6.1: aq. glacial acetic acid / tetrahydrofuran / 8 h / 20 °C

7.1: 84 percent / CrO₃; aq. H₂SO₄ / acetone / 1.5 h

With chromium(VI) oxide; potassium hydroxide; sulfuric acid; sodium hydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; 7.1: Jones oxidation;
DOI:10.1021/jm0495982