Hydrochloric Acid → HCID 68862601, compound

HRID 1725945Notes

Reaction equation

HRID 1725945 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]=1[C:29]([O:31]C)=[O:30])(=[O:17])=[O:16])=[O:8])[CH3:2].O.O.[OH-].[Li+].Cl>O1CCOCC1>[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]=1[C:29]([OH:31])=[O:30])(=[O:17])=[O:16])=[O:8])[CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68864053HCID 68864053, compound

Product 1

HCID 68862601HCID 68862601, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 299A (244 mg, 0.505 mmol) in dioxane (8 mL) and distilled water (4 mL) was treated with lithium hydroxide monohydrate (212 mg, 5.05 mmol), stirred at 60° C. overnight, cooled to room temperature, treated with 1N HCl, and extracted with ethyl acetate two times. The combined organic fractions were washed with brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(+)) m/e 470 (M+H)+; (ESI(−)) m/e 468 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.73 (br s, 1H), 9.10 (br s, 1H), 9.01 (t, 1H), 7.99 (t, 2H), 7.92 (dd, 1H), 7.84 (dd, 1H), 7.76 (dt, 1H), 7.70-7.45 (m, 5H), 3.65 (m, 4H), 3.25 (m, 4H), 1.24 (t, 6H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate two times
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-367d962d868b4d65b4b9ca174f037189
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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