Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl ester

Base Information

Chemical Name:Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl ester
CAS No.:162715-75-5
Molecular Formula:C₂₃H₃₆N₂O₈S
Molecular Weight:500.613
Hs Code.:

Synonyms:Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl ester

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Chemical Property of Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl ester

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Technology Process of Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl ester

There total 9 articles about Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl 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:

: 124-63-0
methanesulfonyl chloride

: 162715-74-4
(3S,5S)-3-((R)-1-Hydroxy-2-methyl-propyl)-5-isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

: 162715-75-5
Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl ester

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -23 ℃; Yield given;
DOI:10.1016/0040-4039(95)00214-W

Reference yield:

: 7517-19-3
methyl (L)-leucinate hydrochloride

: 162715-75-5
Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: DIPEA / acetonitrile / 20 - 60 °C

2.1: 101.5 g / DIPEA / acetonitrile / 24 h / 70 °C

3.1: 93.7 percent / TFA / CH₂Cl₂ / 70 h / 20 °C

4.1: TEA; DCC / CH₂Cl₂ / 20 h / 20 °C

5.1: hydroxylamine / ethanol; tetrahydrofuran / 3 h / 20 °C / pH 6.0

6.1: ethanol; H₂O / Heating

7.1: 54 g / DIPEA / CH₂Cl₂ / 2 h / -40 °C

8.1: LHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -78 °C

8.2: 63.3 percent / 2 h

9.1: 4.5 g / DIPEA; DMAP / CH₂Cl₂ / -23 - 20 °C

With dmap; TEA; hydroxylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo015665d

Reference yield:

: 179678-66-1
N-(1-tert-butoxy-acet-2-yl)-(S)-leucine methyl ester

: 162715-75-5
Methanesulfonic acid (R)-1-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 101.5 g / DIPEA / acetonitrile / 24 h / 70 °C

2.1: 93.7 percent / TFA / CH₂Cl₂ / 70 h / 20 °C

3.1: TEA; DCC / CH₂Cl₂ / 20 h / 20 °C

4.1: hydroxylamine / ethanol; tetrahydrofuran / 3 h / 20 °C / pH 6.0

5.1: ethanol; H₂O / Heating

6.1: 54 g / DIPEA / CH₂Cl₂ / 2 h / -40 °C

7.1: LHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -78 °C

7.2: 63.3 percent / 2 h

8.1: 4.5 g / DIPEA; DMAP / CH₂Cl₂ / -23 - 20 °C

With dmap; TEA; hydroxylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo015665d