N⁶-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N²-[(phenylmethoxy)carbonyl]-L-lysine methyl ester

Base Information

• Chemical Name: N⁶-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N²-[(phenylmethoxy)carbonyl]-L-lysine methyl ester
• CAS No.: 606147-27-7
• Molecular Formula: C₂₃H₃₆N₂O₆
• Molecular Weight: 436.549

Synonyms:N⁶-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N²-[(phenylmethoxy)carbonyl]-L-lysine methyl ester

Chemical Property of N⁶-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N²-[(phenylmethoxy)carbonyl]-L-lysine methyl ester

Chemical Property:

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Technology Process of N⁶-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N²-[(phenylmethoxy)carbonyl]-L-lysine methyl ester

There total 4 articles about N⁶-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N²-[(phenylmethoxy)carbonyl]-L-lysine methyl 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: 92.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-6-methyl-6-amino-2-[[(phenylmethoxy)carbonyl]amino]heptanoic acid methyl ester (606147-26-6) → N6-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N2-[(phenylmethoxy)carbonyl]-L-lysine methyl ester (606147-27-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 20h;

DOI:10.1021/ol0352308

Reference yield:

2,6-dinitro-2,6-dimethyl-3-heptanol (606147-23-3) → N6-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N2-[(phenylmethoxy)carbonyl]-L-lysine methyl ester (606147-27-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / -20 - 20 °C

2: 100 percent / H₂ / (+)-[(COD)Rh-(S,S)-Et-DUPHOS]OTf / methanol / 41 h / 20 °C / 2068.59 Torr

3: 85 percent / acetyl chloride; zinc / methanol / 0 - 55 °C

4: 92 percent / diisopropylethylamine / acetonitrile / 20 h / 20 °C

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; acetyl chloride; zinc; (+)-[(COD)Rh-(S,S)-Et-DUPHOS]OTf; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/ol0352308

Reference yield:

(Z)-6-methyl-6-nitro-2-[[(phenylmethoxy)carbonyl]amino]-2-heptenoic acid methyl ester (606147-24-4) → N6-[2-(1,1-dimethylethoxy)-2-oxoethyl]-6,6-dimethyl-N2-[(phenylmethoxy)carbonyl]-L-lysine methyl ester (606147-27-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂ / (+)-[(COD)Rh-(S,S)-Et-DUPHOS]OTf / methanol / 41 h / 20 °C / 2068.59 Torr

2: 85 percent / acetyl chloride; zinc / methanol / 0 - 55 °C

3: 92 percent / diisopropylethylamine / acetonitrile / 20 h / 20 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; acetyl chloride; zinc; (+)-[(COD)Rh-(S,S)-Et-DUPHOS]OTf; In methanol; acetonitrile;

DOI:10.1021/ol0352308

upstream raw materials:

bromoacetic acid tert-butyl ester

(S)-6-methyl-6-amino-2-[[(phenylmethoxy)carbonyl]amino]heptanoic acid methyl ester

2,6-dinitro-2,6-dimethyl-3-heptanol

(S)-6-methyl-6-nitro-2-[[(phenylmethoxy)carbonyl]amino]heptanoic acid methyl ester

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