Potassium Carbonate → Ethyl 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-hydroxypropanoate

HRID 393552Notes

Reaction equation

HRID 393552 reaction equation
CS([O:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][CH2:10][CH2:9]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[OH:24][CH:25]([CH2:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[S:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:8]([CH2:7][CH2:6][O:5][C:35]2[CH:34]=[CH:33][C:32]([CH2:31][CH:25]([OH:24])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:37][CH:36]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 99216342-(3,4-dihydro-2H-benzo[b][1,4]thiazin-4-yl)ethyl methanesulfonateHCID 21930973Ethyl p-hydroxyphenyllactate

Product 1

HCID 9800403Ethyl 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-hydroxypropanoateYield 17%

Procedure

The title compound (1.9 g, 17%) was prepared as a gummy liquid from 2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethyl methanesulfonate (8.2 g, 30.0 mmol), potassium carbonate (20.7 g, 150 mmol) and ethyl 2-hydroxy-3-(4-hydroxyphenyl)propanoate (6.3 g, 30.0 mmol) using conditions analogous to that described in preparation 2.

Workup

  1. customthat described in preparation 2

Sources & evidence

ORD record
ord-3cc15b52423b4c52a0383e15d5f8f7b6
Source dataset
uspto-grants-2004_10
Patent number
US06809095B2

Reaction notes

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