(2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid

Base Information

Chemical Name:(2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid
CAS No.:916675-84-8
Molecular Formula:C₁₅H₁₉Cl₂NO₄
Molecular Weight:348.226
Hs Code.:

Synonyms:(2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid

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Chemical Property of (2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid

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Technology Process of (2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid

There total 15 articles about (2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid 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: 65.0%

: 916675-81-5
(2S,4S)-2-[(benzyloxycarbonyl)amino]-5,5-dichloro-4-methylpentanoic acid

: 74-88-4
methyl iodide

: 916675-84-8
(2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid

Guidance literature:: With sodium hydride; In acetonitrile; at 20 ℃; for 24h;
DOI:10.1021/ol062279f

Reference yield:

: 916675-70-2
(2S,4S)-2-((tert-butoxycarbonyl)amino)-4-methylpentane-1,5-dioic acid 1-tert-butyl 5-allyl diester

: 916675-84-8
(2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 92 percent / DMAP / acetonitrile / 72 h / 20 °C

2: 77 percent / Pd(PPh₃)4; NaBH₄ / tetrahydrofuran

3: 96 percent / BH₃*SMe₂ / tetrahydrofuran; diethyl ether / 2 h

4: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -45 °C

5: 100 percent / N₂H₄*H₂O / methanol / 3 h

6: 1.54 g / CuCl₂; Et₃N / methanol / 3 h

7: 100 percent / CF₃CO₂H / 1 h

8: 54 percent / NaHCO₃ / dioxane; H₂O / 0 - 20 °C

9: 65 percent / NaH / acetonitrile / 24 h / 20 °C

With dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dimethylsulfide borane complex; sodium hydride; sodium hydrogencarbonate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; copper dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetonitrile; 4: Swern oxidation;
DOI:10.1021/ol062279f

Reference yield:

: 916675-75-7
(2S,4S)-2-(di(tert-butoxycarbonyl)amino)-4-methyl-6-oxohexanoic acid tert-butyl ester

: 916675-84-8
(2S,4S)-2-[N-(benzyloxycarbonyl)-N-methylamino]-5,5-dichloro-4-methylpentanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 65 percent / tert-butylamine; N-chlorosuccinimide; molecular sieves 4 Angstroem / CCl₄ / 1 h / 20 °C

2: 72 percent / NaClO₂; KH₂PO₄; H₂O₂ / acetonitrile; H₂O / 2 h / 0 °C

3: 58 percent / lead tetraacetate; 1,4-cyclohexadiene / benzene / 3 h / 60 °C

4: 100 percent / CF₃CO₂H / 1 h

5: 54 percent / NaHCO₃ / dioxane; H₂O / 0 - 20 °C

6: 65 percent / NaH / acetonitrile / 24 h / 20 °C

With lead(IV) acetate; sodium chlorite; potassium dihydrogenphosphate; N-chloro-succinimide; cyclohexa-1,4-diene; 4 A molecular sieve; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; tert-butylamine; trifluoroacetic acid; In 1,4-dioxane; tetrachloromethane; water; acetonitrile; benzene;
DOI:10.1021/ol062279f