Acetic Acid → HCID 86725280, compound

HRID 576655Notes

Reaction equation

HRID 576655 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[CH2:26][NH2:27])[C:6]([NH:8][C@H:9]1[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:12]=2[O:11][B:10]1[OH:22])=[O:7].CC(O)=O.[CH3:32][C:33]([CH3:35])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[NH2:27][CH2:26][C:25]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:12]=3[O:11][B:10]2[OH:22])=[O:7])=[CH:4][C:3]=1[CH2:2][NH:1][CH:33]([CH3:35])[CH3:32]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 76073617HCID 76073617, compound

Product 1

HCID 86725280HCID 86725280, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-3-(3,4-bis(aminomethyl)benzamido)-2-hydroxy-3,4-dihydro-2H-benzo[e][1,2]oxaborinine-8-carboxylic acid from Example 14 (44.1 mg) in methanol (2 mL) was added TEA (0.042 mL), AcOH (0.050 mL), acetone (0.030 mL), and sodium triacetoxyborohydride (70 mg). The resulting reaction mixture was stirred at room temperature for overnight. After removal of the solvents, the product was then purified by reverse phase HPLC and dried using lyophilization. ESI-MS m/z 412 (MH)+.

Workup

  1. customThe resulting reaction mixture
  2. customAfter removal of the solvents
  3. customthe product was then purified by reverse phase HPLC
  4. customdried

Sources & evidence

ORD record
ord-975890154af84663b4f250323c6a5927
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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