3-(tert-Butyldimethylsilyloxy)phenylboronic Acid → 2-Tert-butyl-5-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

HRID 724614Notes

Reaction equation

HRID 724614 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].[Si:14]([O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>>[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([O:21][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[CH:23]=2)[S:6]1(=[O:13])=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 34630293-(tert-Butyldimethylsilyloxy)phenylboronic AcidHCID 218786382-Tert-butyl-5-chloro-2,3-dihydro-1lambda6,2-thiazole-1,1,3-trione

Product 1

HCID 587468592-Tert-butyl-5-[3-(tert-butyl-dimethyl-silanyloxy)-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 3-(t-butyldimethylsilyoxy)phenylboronic acid as the starting materials. 1H NMR (500 MHz, CDCl3): δ 7.37–7.36 (m, 2H), 7.25–7.24 (m, 1H), 7.03–7.01 (m, 1H), 6.61 (s, 1H), 1.73 (s, 9H), 0.99 (s, 9H), 0.23 (s, 6H); LCMS found for C19H29NO4SSi (M+H)+: m/z=418.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-a48b62903fb3461cbd95e5e4e764616c
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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