(S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

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Chemical Name:(S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester
CAS No.:254750-79-3
Molecular Formula:C₃₃H₃₇F₄N₃O₇
Molecular Weight:663.666
Hs Code.:

(S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

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Chemical Property of (S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

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Technology Process of (S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

There total 8 articles about (S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl 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:

: 168319-04-8
(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester

: 254750-79-3
(S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaI / acetone / 20 °C

2: NaBH₄ / methanol; tetrahydrofuran / 0 °C

3: H₂ / Pd/C / methanol / 4 h / 20 °C / 760 Torr

4: HATU; DIEA / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1016/j.bmcl.2003.12.106

Reference yield:

: Z-Val-Asp(O-tBu)-OH

: 254750-79-3
(S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: ClCO₂iBu; NMM / tetrahydrofuran / 0.5 h / -10 °C

1.2: diethyl ether / 1 h / 0 °C

2.1: aq. HBr / tetrahydrofuran / 0.25 h / 0 - 20 °C

3.1: NaI / acetone / 20 °C

4.1: NaBH₄ / methanol; tetrahydrofuran / 0 °C

5.1: H₂ / Pd/C / methanol / 4 h / 20 °C / 760 Torr

6.1: HATU; DIEA / CH₂Cl₂ / 2 h / 20 °C

With 4-methyl-morpholine; sodium tetrahydroborate; hydrogen bromide; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium iodide; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1016/j.bmcl.2003.12.106

Reference yield:

: (S)-3-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-5-diazo-4-oxo-pentanoic acid tert-butyl ester

: 254750-79-3
(S)-4-Hydroxy-3-{(S)-3-methyl-2-[(naphthalen-1-ylmethyl)-aminooxalyl]-amino}-butyrylamino)-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: aq. HBr / tetrahydrofuran / 0.25 h / 0 - 20 °C

2: NaI / acetone / 20 °C

3: NaBH₄ / methanol; tetrahydrofuran / 0 °C

4: H₂ / Pd/C / methanol / 4 h / 20 °C / 760 Torr

5: HATU; DIEA / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; hydrogen bromide; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1016/j.bmcl.2003.12.106