Triisopropyl borate → Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

HRID 257568Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[B:20]([OH:25])[OH:21])(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 21531Triisopropyl borate

HCID 314059N-(1,1-Dimethylethyl)benzenesulfonamide

HCID 178418339Butyllithium

Product 1

HCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

Procedure

By the method described in Example 10, Step B, N-t-butylbenzenesulfonamide [G. Lombardino, J. Org. Chem., 36, 1843 (1971)] was deprotonated with n-butyllithium, and the resulting dianion was reacted with triisopropyl borate and worked up with acid to give the title compound, which was used directly in the next step without further purification.

Sources & evidence

ORD record: ord-45a3114f918c4e9b96cbd287d3a35cb3
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262412

Reaction notes

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