(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

Base Information

Chemical Name:(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester
CAS No.:1345261-76-8
Molecular Formula:C₃₁H₂₇F₅N₂O₆
Molecular Weight:618.557
Hs Code.:

Synonyms:(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

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Chemical Property of (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

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Technology Process of (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

There total 6 articles about (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl 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: 66.0%

: 14533-84-7
pentafluorophenyl trifloroacetate

: 267230-44-4
(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid

: 1345261-76-8
(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/j.bmcl.2011.08.079

Reference yield:

: (R)-4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

: 1345261-76-8
(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: acetic acid / ethanol / 20 °C

2: sodium cyanoborohydride / 75 °C

3: hydrogenchloride / ethyl acetate / 0 °C

4: water; lithium hydroxide / tetrahydrofuran; methanol / 0 °C

5: palladium on activated charcoal; hydrogen / ethanol / 20 °C

6: sodium hydrogencarbonate / water; acetone

7: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C

With hydrogenchloride; palladium on activated charcoal; water; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1016/j.bmcl.2011.08.079

Reference yield:

: C₂₀H₂₈N₂O₄

: 1345261-76-8
(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: sodium cyanoborohydride / 75 °C

2: hydrogenchloride / ethyl acetate / 0 °C

3: water; lithium hydroxide / tetrahydrofuran; methanol / 0 °C

4: palladium on activated charcoal; hydrogen / ethanol / 20 °C

5: sodium hydrogencarbonate / water; acetone

6: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C

With hydrogenchloride; palladium on activated charcoal; water; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1016/j.bmcl.2011.08.079