N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester

Base Information

Chemical Name:N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester
CAS No.:159487-59-9
Molecular Formula:C₃₉H₆₁N₃O₁₀
Molecular Weight:731.927
Hs Code.:

Synonyms:N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester

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Chemical Property of N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester

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Technology Process of N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester

There total 14 articles about N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl 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: 72.0%

: 77902-89-7
benzyl <(trifluoromethyl)sulfonyloxy>acetate

: 159487-57-7
N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>amine

: 159487-59-9
N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; 1.) -20 deg C to -15 deg C, 4 h, 2.) r.t., 1 h;
DOI:10.1021/jo00092a022

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 159487-59-9
N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: i-Pr₂NEt / acetonitrile / 1.) 0 deg C, 30 min, 2.) r.t., 9 h

2: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 2.5 h / 0 °C

3: 95 percent / NaN₃ / dimethylformamide / 8 h / Heating

4: 99 percent / H₂ / 10percent Pd/C / methanol / 0.5 h / 2585.7 Torr

5: CH₂Cl₂ / 40 h / 0 °C

6: H₂ / 10percent Pd/C / methanol / 1.5 h

7: i-Pr₂NEt / acetonitrile / 1.) -10 to -5 deg C, 3.5 h, 2.) r.t., 1 h

8: 72 percent / i-Pr₂NEt / acetonitrile / 1.) -20 deg C to -15 deg C, 4 h, 2.) r.t., 1 h

With sodium azide; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00092a022

Reference yield:

: 72289-52-2
(2S,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester

: 159487-59-9
N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: i-Pr₂NEt / CH₂Cl₂ / 1.) -30 deg C, 45 min, 2.) 0 deg C, 15 min

2: CH₂Cl₂ / 40 h / 0 °C

3: H₂ / 10percent Pd/C / methanol / 1.5 h

4: i-Pr₂NEt / acetonitrile / 1.) -10 to -5 deg C, 3.5 h, 2.) r.t., 1 h

5: 72 percent / i-Pr₂NEt / acetonitrile / 1.) -20 deg C to -15 deg C, 4 h, 2.) r.t., 1 h

With hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00092a022