(3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid
• CAS No.: 346610-79-5
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507
• Mol file: 346610-79-5.mol

Synonyms:(3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxycarbonylpyrrolidine

Chemical Property of (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

(3S,4R)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid

There total 7 articles about (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic 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:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (3S,4R)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester; hydrochloride → (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxycarbonylpyrrolidine (346610-79-5)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 0 - 20 ℃;

DOI:10.1021/jo001534l

Reference yield:

(3S,4R)-4-((S)-1-Phenyl-ethylamino)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester; hydrochloride → (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxycarbonylpyrrolidine (346610-79-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / ethanol; H₂O / 24 h / 2327.23 Torr

2: NaHCO₃ / H₂O; acetone / 0 - 20 °C

With hydrogen; sodium hydrogencarbonate; In ethanol; water; acetone;

DOI:10.1021/jo001534l

Reference yield:

C20H28N2O4 → (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxycarbonylpyrrolidine (346610-79-5)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride / ethyl acetate / 0 °C

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

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

4: sodium hydrogencarbonate / water; acetone

With hydrogenchloride; palladium on activated charcoal; water; hydrogen; sodium hydrogencarbonate; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; acetone;

DOI:10.1016/j.bmcl.2011.08.079

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

4-amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

(3R,4S)-1-(N-tert-butoxycarbonyl)-3-[(1'S)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride

Downstream raw materials:

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

(3R,4S)-1-(2,2,2-trifluoroacetyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

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