(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione

Base Information

Chemical Name:(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione
CAS No.:162715-76-6
Molecular Formula:C₂₂H₃₂N₂O₅
Molecular Weight:404.506
Hs Code.:

Synonyms:(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione

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Chemical Property of (S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione

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Technology Process of (S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione

There total 10 articles about (S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione 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:

: 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

: 162715-77-7
(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(Z)-ylidene]-piperazine-2,6-dione

: 162715-76-6
(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 0 - 20 ℃; for 2h;
DOI:10.1016/0040-4039(95)00214-W

Reference yield:

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

: 162715-76-6
(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione

Guidance literature:: Multi-step reaction with 10 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

10.1: 400 mg / DBU / toluene / 0 - 50 °C

With dmap; TEA; hydroxylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo015665d

Reference yield:

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

: 162715-76-6
(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(E)-ylidene]-piperazine-2,6-dione

Guidance literature:: Multi-step reaction with 9 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

9.1: 400 mg / DBU / toluene / 0 - 50 °C

With dmap; TEA; hydroxylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo015665d