Hydrochloric Acid → HCID 67174690, compound

HRID 1256089Notes

Reaction equation

HRID 1256089 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][CH2:23][C:24](=[O:26])[CH3:25])[CH:3]=1.[BH4-].[Na+].Cl>CO>[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:9])=[O:10])=[C:4]([CH2:22][CH2:23][CH:24]([OH:26])[CH3:25])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 53234367HCID 53234367, compound

Product 1

HCID 67174690HCID 67174690, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(3-oxobutyl)benzenesulfonamide (0.42 g, 1 mmol) in MeOH (15 mL) was added NaBH4 (0.13 g, 3 mmol). The mixture was stirred at r.t. for 2 hrs. The reaction mixture was concentrated, the residue was purified by pre-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 5%-33%, 23 min), concentrated, acidified with HCl and freeze-dried to give 4-amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(3-hydroxybutyl)benzenesulfonamide (230 mg, yield 55%) as HCl salt. 1H NMR: (400 MHz, DMSO-d6): δ 9.90 (s, 1H), 7.56 (d, 1H), 7.42 (d, 1H), 7.22 (d, 1H), 7.13-7.10 (m, 1H), 6.42 (d, 1H), 6.36-6.33 (m, 1H), 4.85 (s, 2H), 3.69-3.65 (m, 1H), 2.87-2.80 (m, 2H), 1.55-1.49 (m, 2H), 1.08 (d, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by pre-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 5%-33%, 23 min)
  3. concentrationconcentrated
  4. customfreeze-dried

Sources & evidence

ORD record
ord-37b2dfc9ba6443c6856579dfccb60ea5
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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