4-Oxo-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]butanoic acid → HCID 25069443, compound

HRID 1035617Notes

Reaction equation

HRID 1035617 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:19].[O:20]=[C:21]([NH:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=1)[CH2:22][CH2:23][C:24]([OH:26])=[O:25]>>[OH:19][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[CH:7]=2)[C:2]=1[C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:21](=[O:20])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 27346544-Oxo-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]butanoic acidHCID 24950391HCID 24950391, compound

Product 1

HCID 25069443HCID 25069443, compoundYield 12%

Procedure

The compound is prepared by the reaction of 1-bromo-6-(3-hydroxyphenyl)-naphthalene-2-ol (100 mg, 0.32 mmol, 1 eq) with 4-oxo-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)butanoic acid (101.3 mg, 0.32 mmol, 1 eq) according to method A in 10 min. Purification by column chromatography with dichloromethane/methanol 90/10 yields the desired compound in a yield of 12%, 16 mg.

Workup

  1. customPurification by column chromatography with dichloromethane/methanol 90/10

Sources & evidence

ORD record
ord-8e458c8c99654a3f92a546d4b9b43a29
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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