methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate

Base Information

Chemical Name:methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate
CAS No.:367259-61-8
Molecular Formula:C₂₂H₃₈N₂O₆S
Molecular Weight:458.62
Hs Code.:

Synonyms:methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate

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Chemical Property of methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate

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Technology Process of methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate

There total 4 articles about methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate 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:

: 109183-71-3
N-(tert-butoxycarbonyl)-L-cyclohexylglycine

: (2S,4R)-4-(3-Hydroxy-propylsulfanyl)-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride

: 367259-61-8
methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate

Guidance literature:: With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In dichloromethane; N,N-dimethyl-formamide; at -8 ℃; for 48h;
DOI:10.1021/jo011160b

Reference yield:

: 74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9
(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

: 367259-61-8
methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

2: 78 percent / NaH / dimethylformamide / 0 - 20 °C

3: 4 M HCl / dioxane / 1 h / 0 °C

4: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / 48 h / -8 °C

With 4-methyl-morpholine; hydrogenchloride; dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo011160b

Reference yield:

: 367259-60-7
(2S,4R)-4-[(3-hydroxypropyl)thio]-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester

: 367259-61-8
methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 4 M HCl / dioxane / 1 h / 0 °C

2: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / 48 h / -8 °C

With 4-methyl-morpholine; hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo011160b