[1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: [1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 847978-87-4
• Molecular Formula: C₃₄H₃₉N₃O₅
• Molecular Weight: 569.701

Synonyms:[1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Chemical Property of [1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

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Technology Process of [1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

There total 4 articles about [1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl 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: 98.0%

N-Fmoc L-Phe (35661-40-6) + (2S,4S)-4-tert-Butoxy-pyrrolidine-2-carboxylic acid methylamide → [1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (847978-87-4)

Guidance literature:

With bromo-tris-dimethylamino-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo0490043

Reference yield:

(2S,4S)-4-Hydroxy-2-methylcarbamoyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (847978-69-2) → [1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (847978-87-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / BF₃*Et₂O / CH₂Cl₂; cyclohexane / 2.5 h

2: diethylamine / acetonitrile / 0.5 h / 20 °C

3: 98 percent / diisopropylethylamine; BroP reagent / CH₂Cl₂ / 20 °C

With bromo-tris-dimethylamino-phosphonium hexafluorophosphate; boron trifluoride diethyl etherate; diethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; cyclohexane; acetonitrile;

DOI:10.1021/jo0490043

Reference yield:

Fmoc-cis-4-hyp(OtBu)-NHMe (847978-70-5) → [1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (847978-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: diethylamine / acetonitrile / 0.5 h / 20 °C

2: 98 percent / diisopropylethylamine; BroP reagent / CH₂Cl₂ / 20 °C

With bromo-tris-dimethylamino-phosphonium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo0490043

upstream raw materials:

N-Fmoc L-Phe

(2S,4S)-4-Hydroxy-2-methylcarbamoyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Fmoc-cis-4-hyp(O^tBu)-NHMe

(4S)-Nα-Fmoc-4-hydroxy-L-proline

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