Benzyl chloroformate → HCID 67173846, compound

HRID 1256144Notes

Reaction equation

HRID 1256144 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.[C:24](Cl)([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>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:24](=[O:25])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 671734224-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide

Product 1

HCID 67173846HCID 67173846, compoundYield 52.9%

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 CbzCl (151 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 (220 mg, 42%) as TFA salt. 1H NMR: DMSO 400 MHz δ 9.97 (s, 1H), 7.63 (t, J=7.2 Hz, 1H), 7.55 (q, 1H), 7.42 (q, 1H), 7.37 (q, 3H), 7.32 (q, 3H), 7.30 (q, 3H), 6.52 (s, 1H), 6.37 (q, 1H), 5.05 (s, 2H), 4.83 (s, 2H), 4.53 (s, 2H).

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-0e5c06a5b1de4d4f9849a979fa5a29ad
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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