Cyanogen Bromide → HCID 178508298, compound

HRID 1478837Notes

Reaction equation

HRID 1478837 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[CH2:27][NH2:28])[C:6]([NH:8][C@H:9]([B:21]([OH:23])O)[CH2:10][C:11]1[C:12]([OH:20])=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])=[O:7].Br[C:30]#[N:31]>CN(C=O)C>[NH2:31][C:30]1[NH:1][CH2:2][C:3]2[CH:4]=[C:5]([C:6]([NH:8][C@H:9]3[CH2:10][C:11]4[CH:19]=[CH:18][CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]=4[O:20][B:21]3[OH:23])=[O:7])[CH:24]=[CH:25][C:26]=2[CH2:27][N:28]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 86725249HCID 86725249, compound

Product 1

HCID 178508298HCID 178508298, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (R)-3-(2-(3,4-bis(aminomethyl)benzamido)-2-boronoethyl)-2-hydroxybenzoic acid (10 mg) in DMF (1 mL) was added BrCN (10 mg) and the reaction was stirred for 5 hr. The crude product was purified by reverse phase preparative HPLC and dried using lyophilization. ESI-MS m/z 395 (MH)+.

Workup

  1. customThe crude product was purified by reverse phase preparative HPLC
  2. customdried

Sources & evidence

ORD record
ord-2b9c7e5b3f504af189a0b06d5fddffdd
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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