Isobutyl chloroformate → HCID 67311500, compound

HRID 1256142Notes

Reaction equation

HRID 1256142 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][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26]>C1COCC1>[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][CH2:28][CH:29]([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 671734224-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Product 1

HCID 67311500HCID 67311500, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (500 mg, 0.89 mmol) and TEA (360 mg, 3.6 mmol) in THF (200 mL) at −20° C. was slowly added iso-butyl chloroformate (121 mg, 0.89 mmol) in THF (10 mL). Then the mixture was stirred at room temperature for 2 hrs. The mixture 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 %: 15%-40%, 25 min) to give the title compound (185 mg, 38%) as TFA salt. 1H NMR DMSO 400 MHz δ 9.98 (s, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.43 (q, 2H), 7.20 (d, J=8.8 Hz, 1H), 7.11 (q, 1H), 6.48 (s, 1H), 6.35 (q, 1H), 4.84 (s, 2H), 4.50 (s, 2H), 3.75 (d, J=7.2 Hz, 2H), 1.84 (q, 1H), 0.88 (q, 6H).

Workup

  1. customat −20° C.
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by prep-HPLC (column: Luna 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.025% TFA; B-MeCN] B %: 15%-40%, 25 min)

Sources & evidence

ORD record
ord-d70a4351e38f48c3ab8246c5adbe6047
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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