4-(Hydroxymethyl)benzeneboronic acid → 2-Tert-butyl-5-(4-hydroxymethyl-phenyl)-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

HRID 724591Notes

Reaction equation

HRID 724591 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7](Cl)[S:6]1(=[O:13])=[O:12])([CH3:4])([CH3:3])[CH3:2].[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>>[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][OH:14])=[CH:17][CH:18]=2)[S:6]1(=[O:13])=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 218786382-Tert-butyl-5-chloro-2,3-dihydro-1lambda6,2-thiazole-1,1,3-trione

Product 1

HCID 587465472-Tert-butyl-5-(4-hydroxymethyl-phenyl)-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

Procedure

This compound was prepared according to the procedure of Example 1.1, Step 4, using 9-A and 4-(hydroxymethyl)phenylboronic acid as the starting materials. 1H NMR (500 MHz, CDCl3): δ 7.77 (d, J=8.3 Hz, 2H), 7.52 (d, J=8.3 Hz, 2H), 6.64 (s, 1H), 4.79 (d, J=5.9 Hz, 2H), 1.86–1.84 (m, 1H), 1.73 (s, 9H); LCMS found for C14H17NO4SNa (M+Na)+: m/z=318.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-5b45a7e2709249ffb94467e835e95b93
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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