Hydrochloric Acid → 2-(6-(5-Carbamimidoylthiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

HRID 1798280Notes

Reaction equation

HRID 1798280 reaction equation
[C:1]([C:4]1[S:8][C:7]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([O:21]CC)=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)=[N:6][CH:5]=1)(=[NH:3])[NH2:2].[OH-].[Na+].Cl>CO>[C:1]([C:4]1[S:8][C:7]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([OH:21])=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)=[N:6][CH:5]=1)(=[NH:2])[NH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58292652HCID 58292652, compound

Product 1

HCID 582927242-(6-(5-Carbamimidoylthiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude ethyl 2-(6-(5-carbamimidoylthiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in 6 ml methanol was treated with aqueous NaOH solution (500 mg, 6 ml water) for one hour. It was acidified with 1N HCl to pH 5 and then concentrated. HPLC purification gave desired product as white flakes. 1H NMR (400 MHz, DMSO-d6) δ 12.4 (b, 1H), 9.22 (b, 2H), 9.01 (b, 2H), 8.21 (s, 1H), 7.44 (d, J=2 Hz, 1H), 7.32 (d, J=1.6 Hz, 1H), 5.50 (dd, J=9.2, 2.4 Hz, 1H), 3.05 (dd, J=15.6, 2.4 Hz, 1H), 2.28 (s, 3H), 2.12 (dd, J=15.6, 9.6 Hz, 1H). MS (ESI) m/z=348 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customHPLC purification

Sources & evidence

ORD record
ord-e04cefcf9d344c748d6aab8f8b01bc8f
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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