Lithium Hydroxide → HCID 58292752, compound

HRID 1798284Notes

Reaction equation

HRID 1798284 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([O:10][C:11]2[CH:12]=[C:13]([CH3:27])[C:14]3[CH:18]([CH2:19][C:20]([O:22]CC)=[O:21])[O:17][B:16]([OH:25])[C:15]=3[CH:26]=2)[S:8][CH:9]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[C:20]([CH2:19][CH:18]1[O:17][B:16]([OH:25])[C:15]2[CH:26]=[C:11]([O:10][C:7]3[S:8][CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]=3)[CH:12]=[C:13]([CH3:27])[C:14]1=2)([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67252596HCID 67252596, compound

Product 1

HCID 58292752HCID 58292752, compoundYield 7.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(3-ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-4-carboxylic acid methyl ester (500 mg, 1.28 mmol) in THF (30 mL) was treated with LiOH (107 mg, 2.55 mmol) in water (15 mL) at room temperature for 1 h. The reaction was concentrated to dryness. The residue was diluted with water and adjusted to pH 3. The mixture was purified by preparative HPLC to give the title compound (33 mg). 1H NMR (300 MHz, CD3OD) δ 7.87 (s, 1H), 7.35 (s, 1H), 7.25 (s, 1H), 5.70-5.66 (m, 1H), 3.27-3.10 (m, 1H), 2.39 (s, 3H), 2.36-2.31 (m, 1H). MS found: (M+H)+: 350.1.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. additionThe residue was diluted with water
  3. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-98b7ed0481b24282873f10e9292387e0
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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