4-(2-Piperidin-1-yl-ethoxy)benzyl chloride → 2-Methyl-2-(2-methyl-furan-3-sulfonyl)-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-propionic acid

HRID 1595584Notes

Reaction equation

HRID 1595584 reaction equation
C(OC(=O)C(S(C1C=COC=1C)(=O)=O)C)C.ClCC1C=CC(OCCN2CCCCC2)=CC=1.[CH2:34]([O:36][C:37](=[O:65])[C:38]([CH3:64])([S:55]([C:58]1[CH:62]=[CH:61][O:60][C:59]=1[CH3:63])(=[O:57])=[O:56])[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][N:49]2[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]2)=[CH:42][CH:41]=1)[CH3:35]>C(O)C.[OH-].[Na+]>[CH2:34]([O:36][C:37](=[O:65])[C:38]([CH3:64])([S:55]([C:58]1[CH:62]=[CH:61][O:60][C:59]=1[CH3:63])(=[O:57])=[O:56])[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][N:49]2[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]2)=[CH:42][CH:41]=1)[CH3:35].[CH3:64][C:38]([S:55]([C:58]1[CH:62]=[CH:61][O:60][C:59]=1[CH3:63])(=[O:57])=[O:56])([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][N:49]2[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]2)=[CH:42][CH:41]=1)[C:37]([OH:65])=[O:36]

Participants

7

Reactant 3

HCID 98607864-(2-Piperidin-1-yl-ethoxy)benzyl chlorideHCID 536590482-Methyl-2-(2-methyl-furan-3-sulfonyl)-3-[4-(2-piperidin-yl-ethoxy)-phenyl]-propionic acid ethyl esterHCID 539607372-(2-Methyl-furan-3-sulfonyl)-propionic acid ethyl ester

Product 2

HCID 184169162-Methyl-2-(2-methyl-furan-3-sulfonyl)-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-propionic acidHCID 536590482-Methyl-2-(2-methyl-furan-3-sulfonyl)-3-[4-(2-piperidin-yl-ethoxy)-phenyl]-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Methyl-2-(2-methyl-furan-3-sulfonyl)-3-[4-(2-piperidin-yl-ethoxy)-phenyl]-propionic acid ethyl ester was prepared according to the general method as outlined in example 9. Starting from 2-(2-methyl-furan-3-sulfonyl)-propionic acid ethyl ester (2.4 g, 9.8 mmol) and 1-[2-(4-chloromethylphenoxy)-ethyl]-piperidine (2.96 g, 10.7 mmol); Yield 2.4 g (92%); amber oil; MS 464.2 (M+H)+. 2-Methyl-2-(2-methyl-furan-3-sulfonyl)-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-propionic acid was prepared according to the general method as outlined in example 1. Starting from 2-methyl-2-(2-methyl-furan-3-sulfonyl)-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-propionic acid ethyl ester (2.01 g, 4.5 mmol), dissolved in ethanol (20 mL) and 10 N sodium hydroxide (10 mL). The resulting mixture was worked up as outline in example 9. Yield 2.03 g; amber crystals mp 66-68° C.; MS 434 (M−H).

Sources & evidence

ORD record
ord-f16f0ac4ca464c60bc4876bf78bd9c6c
Source dataset
uspto-grants-2001_09
Patent number
US06288086B1

Reaction notes

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