3-Aminophenylboronic acid → 3-Aminophenylboronic acid

HRID 420427Notes

Reaction equation

HRID 420427 reaction equation
[CH2:1]1[S:5][C@@H:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]N2C(=O)C(S([O-])(=O)=O)CC2=O)=[O:11])[C@H:3]2[NH:24][C:25]([NH:27][C@@H:2]12)=[O:26].[Na+].[NH2:29][C:30]1[CH:31]=[C:32]([B:36]([OH:38])[OH:37])[CH:33]=[CH:34][CH:35]=1>>[OH:12][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:4]1[C@@H:3]2[C@@H:2]([NH:27][C:25]([NH:24]2)=[O:26])[CH2:1][S:5]1)=[O:11].[NH2:29][C:30]1[CH:31]=[C:32]([B:36]([OH:38])[OH:37])[CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 56846292Sodium 2,5-dioxo-1-({5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}oxy)pyrrolidine-3-sulfonate

Product 2

HCID 922693-Aminophenylboronic acidHCID 171548Biotin

Procedure

The reaction scheme is illustrated in FIG. 6. FIG. 7 shows IR spectra of the reactants sulfo-NHS-biotin (top) and m-aminophenylboronic acid (middle), and the non-purified reaction mixture after stirring (bottom), comprising the reaction product (i.e. the compound with formula (II)). The bottom spectrum shows an additional vibration at about 1685 cm-1 (indicated with an arrow in FIG. 7) which can be attributed to the amide bond formed between biotin and m-aminophenylboronic acid.

Workup

  1. customThe reaction scheme

Sources & evidence

ORD record
ord-ec71eaa44c2d4c7abee569f9ce61b65e
Source dataset
uspto-grants-2012_01
Patent number
US08097463B2

Reaction notes

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