Methyl chloroformate → HCID 86655220, compound

HRID 1256138Notes

Reaction equation

HRID 1256138 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]3[CH2:19][O:18][B:17]([OH:20])[C:16]=3[CH:21]=2)(=[O:10])=[O:9])=[C:4]([CH2:22][NH2:23])[CH:3]=1.Cl[C:25]([O:27][CH3:28])=[O:26]>N1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](=[O:9])(=[O:10])[NH:11][C:12]2[CH:13]=[CH:14][C:15]3[CH2:19][O:18][B:17]([OH:20])[C:16]=3[CH:21]=2)=[C:4]([CH:3]=1)[CH2:22][NH:23][C:25](=[O:26])[O:27][CH3:28].[OH:20][B:17]1[C:16]2[CH:21]=[C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:25](=[O:26])[O-:27])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH:13]=[CH:14][C:15]=2[CH2:19][O:18]1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 671734224-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Product 2

HCID 67174325HCID 67174325, compoundYield 21.28%HCID 86655220HCID 86655220, compoundYield 39.64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (832.5 mg, 2.5 mmol) in pyridine (20 ml) was stirred at room temperature for 30 mins. Methyl chloroformate (708.5 mg, 7.5 mmol) was then added to the mixture and it was stirred at room temperature for overnight. The solution was concentrated in vacuo and the residue was purified by prep. HPLC (column: Luna 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.025% TFA; B-MeCN] B %: 5%-45%, 30 min) to give methyl 5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)benzylcarbamate (208 mg, 21.28%) as a yellow solid and methyl 3-(methoxycarbonylamino)methyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenylcarbamate (445 mg, 39.64%) as an orange solid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-2b30cd2074a44e9fa126dde15ba14163
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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