HCID 58292863, compound → 2-(3-Ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-5-carboxylic acid

HRID 1798286Notes

Reaction equation

HRID 1798286 reaction equation
C([O:5][C:6]([C:8]1[S:12][C:11]([O:13][C:14]2[CH:15]=[C:16]([CH3:30])[C:17]3[CH:21]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:20][B:19]([OH:28])[C:18]=3[CH:29]=2)=[N:10][CH:9]=1)=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[CH2:26]([O:25][C:23]([CH2:22][CH:21]1[O:20][B:19]([OH:28])[C:18]2[CH:29]=[C:14]([O:13][C:11]3[S:12][C:8]([C:6]([OH:7])=[O:5])=[CH:9][N:10]=3)[CH:15]=[C:16]([CH3:30])[C:17]1=2)=[O:24])[CH3:27]

Participants

3

Reactant 1

HCID 58292863HCID 58292863, compound

Product 1

HCID 582928242-(3-Ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-5-carboxylic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(3-Ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-5-carboxylic acid tert-butyl ester (3.3 g, 7.6 mmol) was treated with TFA (40 mL) and stirred at room temperature for overnight. The reaction mixture was concentrated and purified by column chromatography (silica, DCM/MeOH=20:1) affording the title compound (2.5 g, 87%) as a white foam. 1H NMR (CDCl3) δ 7.98 (s, 1H), 7.45 (d, 1H), 7.19 (d, 1H), 5.67 (dd, 1H), 4.20 (q, 2H), 3.12 (dd, 1H), 2.43 (m, 1H), 2.39 (s, 3H), 1.56 (s, 9H), 1.24 (t, 3H). MS found: (M+H)+: 378.05.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography (silica, DCM/MeOH=20:1)

Sources & evidence

ORD record
ord-c1a9ccb04339404390ba176c12f16ec5
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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