3-Methoxypropyl 4-methylbenzenesulfonate → (R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-[2,6-difluoro-3-(3-methoxy-propoxy)-benzyl]ester

HRID 1794155Notes

Reaction equation

HRID 1794155 reaction equation
[F:1][C:2]1[C:26]([OH:27])=[CH:25][CH:24]=[C:23]([F:28])[C:3]=1[CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@H:9]1[CH2:21][CH3:22])=[O:7].[CH3:29][O:30][CH2:31][CH2:32][CH2:33]OS(C1C=CC(C)=CC=1)(=O)=O>>[F:1][C:2]1[C:26]([O:27][CH2:33][CH2:32][CH2:31][O:30][CH3:29])=[CH:25][CH:24]=[C:23]([F:28])[C:3]=1[CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][C@H:9]1[CH2:21][CH3:22])=[O:7]

Participants

3

Reactant 2

HCID 135229883-Methoxypropyl 4-methylbenzenesulfonateHCID 69142665(R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(2,6-difluoro-3-hydroxy-benzyl)ester

Product 1

HCID 69140559(R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-[2,6-difluoro-3-(3-methoxy-propoxy)-benzyl]esterYield 97%

Procedure

This compound was prepared from (R)-2-ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(2,6-difluoro-3-hydroxy-benzyl) ester and toluene-4-sulfonic acid 3-methoxy-propyl ester according to the procedure described in Example 207 to give the product as a colorless oil (117 mg; 97%); MS (ISP): 490.4 (M+NH4)+.

Sources & evidence

ORD record
ord-c9b0914725f246088a61dfda67acc53f
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…