(R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate

Base Information

Chemical Name:(R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate
CAS No.:369378-01-8
Molecular Formula:C₂₃H₂₄Cl₂N₂O₆S₂
Molecular Weight:559.491
Hs Code.:

Synonyms:(R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate

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Chemical Property of (R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate

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Technology Process of (R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate

There total 8 articles about (R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate 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: 75.0%

: 98-59-9
p-toluenesulfonyl chloride

: 369377-99-1
(R)-4-chloro-N-[2-(6-chloropyridin-2-yl)-2,3-dihydroxypropyl]-3,N-dimethylbenzenesulfonamide

: 369378-01-8
(R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate

Guidance literature:: With pyridine; at 0 ℃; for 8h;
DOI:10.1271/bbb.65.1482

Reference yield:

: 118775-50-1
2-chloro-6-(1-chloromethylvinyl)pyridine

: 369378-01-8
(R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 35.5 g / HOAc / 24 h / 100 °C

2.1: 90 percent / Et₃N; H₂O / methanol / 3 h / Heating

3.1: Ti(O-i-Pr)2Cl₂; D-(+)-diethyl tartrate / CH₂Cl₂ / 0.33 h / 20 °C

3.2: t-butyl hydroperoxide / CH₂Cl₂ / 48 h / -20 °C

4.1: aq. NaOH / diethyl ether / 0.5 h / 0 - 5 °C

5.1: 70 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 64 percent / tetra-N-butylammonium bromide; aq. NaOH / toluene / 3.5 h / 100 °C

7.1: 77 percent / p-toluenesulfonic acid / methanol / 0.75 h / 20 °C

8.1: 75 percent / pyridine / 8 h / 0 °C

With pyridine; sodium hydroxide; titanium(IV) dichlorodiisopropylate; D-(+)-diethyl tartrate; tetrabutylammomium bromide; water; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; diethyl ether; dichloromethane; toluene; 3.1: Sharpless asymmetric chlorohydroxylation / 3.2: Sharpless asymmetric chlorohydroxylation;
DOI:10.1271/bbb.65.1482

Reference yield:

: 369377-89-9
2-(6-chloropyridin-2-yl)prop-2-en-1-ol

: 369378-01-8
(R)-3-[(4-chloro-3-methylbenzenesulfonyl)methylamino]-2-(6-chloropyridin-2-yl)-2-hydroxypropyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: Ti(O-i-Pr)2Cl₂; D-(+)-diethyl tartrate / CH₂Cl₂ / 0.33 h / 20 °C

1.2: t-butyl hydroperoxide / CH₂Cl₂ / 48 h / -20 °C

2.1: aq. NaOH / diethyl ether / 0.5 h / 0 - 5 °C

3.1: 70 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 64 percent / tetra-N-butylammonium bromide; aq. NaOH / toluene / 3.5 h / 100 °C

5.1: 77 percent / p-toluenesulfonic acid / methanol / 0.75 h / 20 °C

6.1: 75 percent / pyridine / 8 h / 0 °C

With pyridine; sodium hydroxide; titanium(IV) dichlorodiisopropylate; D-(+)-diethyl tartrate; tetrabutylammomium bromide; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; toluene; 1.1: Sharpless asymmetric chlorohydroxylation / 1.2: Sharpless asymmetric chlorohydroxylation;
DOI:10.1271/bbb.65.1482