Water → HCID 68863967, compound

HRID 1725922Notes

Reaction equation

HRID 1725922 reaction equation
[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([NH:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[C:28]([O:30]C)=[O:29])(=[O:16])=[O:15])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[OH-].[Li+]>O1CCOCC1>[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([NH:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[C:28]([OH:30])=[O:29])(=[O:16])=[O:15])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrate2×HCID 68866216HCID 68866216, compound

Product 1

HCID 68863967HCID 68863967, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 171A (30.7 mg, 0.070 mmol) in dioxane (1.0 mL) and distilled water (0.5 mL) was treated with lithium hydroxide monohydrate (9.0 mg, 0.21 mmol), stirred overnight at 60° C., treated with additional lithium hydroxide monohydrate (15.0 mg, 0.357 mmol), heated to 60° C. for an additional three days, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(+)) m/e 425 (M+H)+, 447 (M+Na)+; (ESI(−)) m/e 423 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.73 (br s, 1H), 8.10 (d, 1H), 7.96 (d, 1H), 7.89 (d, 2H), 7.70 (dt, 1H), 7.54 (m, 5H), 3.49 (t, 2H), 3.04 (t, 2H), 1.86 (q, 2H), 1.70 (t, 2H).

Workup

  1. temperatureheated to 60° C. for an additional three days
  2. concentrationconcentrated
  3. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2b184b4749984c9c8839e13893a85f4a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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