(3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

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Chemical Name:(3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione
CAS No.:179679-01-7
Molecular Formula:C₂₈H₂₉FN₂O₆
Molecular Weight:508.546
Hs Code.:

Synonyms:(3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

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Chemical Property of (3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

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Technology Process of (3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

There total 8 articles about (3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-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: 64.5%

: 459-57-4
4-fluorobenzaldehyde

: 179678-73-0
1-methoxymethoxy-3S-benzyl-4-p-methoxybenzylpiperazine-2,6-dione

: 179679-01-7
(3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

Guidance literature:: 1-methoxymethoxy-3S-benzyl-4-p-methoxybenzylpiperazine-2,6-dione; With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 3h;

4-fluorobenzaldehyde; for 2h; Further stages.;
DOI:10.1021/jo015665d

Reference yield:

: 7524-50-7
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

: 179679-01-7
(3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: DIPEA / acetonitrile / 6 h

2.1: 34.0 g / DIPEA / acetonitrile / 70 °C

3.1: TFA / CH₂Cl₂ / 48 h / 20 °C

4.1: TEA; DCC / CH₂Cl₂ / 20 h / 20 °C

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

6.1: 25 g / ethanol; H₂O / 48 h / Heating

7.1: 57.8 percent / DIPEA / CH₂Cl₂ / -40 °C

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

8.2: 64.5 percent / 2 h

With TEA; hydroxylamine hydrochloride; 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:

: 227623-99-6
2-(tert-butoxycarbonylmethyl-amino)-3-phenyl-propionic acid methyl ester

: 179679-01-7
(3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: 34.0 g / DIPEA / acetonitrile / 70 °C

2.1: TFA / CH₂Cl₂ / 48 h / 20 °C

3.1: TEA; DCC / CH₂Cl₂ / 20 h / 20 °C

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

5.1: 25 g / ethanol; H₂O / 48 h / Heating

6.1: 57.8 percent / DIPEA / CH₂Cl₂ / -40 °C

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

7.2: 64.5 percent / 2 h

With TEA; hydroxylamine hydrochloride; 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