N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester
• CAS No.: 160233-05-6
• Molecular Formula: C₂₆H₃₆N₂O₇S
• Molecular Weight: 520.647

Synonyms:N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester

Chemical Property of N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester

There total 2 articles about N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic 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: 81.0%

benzo[1,3]dioxol-5-sulfonyl chloride (115010-10-1) + (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol (160232-08-6) → N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester (160233-05-6)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1128/AAC.01413-06

Reference yield:

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) → N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester (160233-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 3 h / 80 °C

2: aq. Na₂CO₃ / CH₂Cl₂ / 0 - 20 °C

With sodium carbonate; In ethanol; dichloromethane;

DOI:10.1021/jm060666p

Reference yield: 82.0%

N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester (160233-05-6) + 1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione (253265-97-3) → GRL-98065

Guidance literature:

N-[(1S,2R)-3-[[(benzo-[1,3]-dioxole-5-sulfonyl)](isobutyl)amino]-1-benzyl-2-hydroxypropyl]carbamic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

1-[[[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl]oxy]pyrrolidine-2,5-dione; With triethylamine; In acetonitrile; at 20 ℃; for 4h; Further stages.;

DOI:10.1128/AAC.01413-06

upstream raw materials:

benzo[1,3]dioxol-5-sulfonyl chloride

(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

Downstream raw materials:

N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzo[d][1,3]dioxole-5-sulfonamide

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