Hydrochloric Acid → HCID 9958164, compound

HRID 273265Notes

Reaction equation

HRID 273265 reaction equation
C([O:3][C:4](=[O:36])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH:32]=[O:33])=[CH:26][C:25]=2[O:34][CH3:35])=[CH:20][CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])C.[Li+].[OH-].OO.Cl.[CH2:42]1COC[CH2:43]1>>[Cl:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=1[C:7]([NH:6][C@H:5]([C:4]([OH:3])=[O:36])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH2:32][O:33][CH2:42][CH3:43])=[CH:26][C:25]=2[O:34][CH3:35])=[CH:22][CH:23]=1)=[O:16]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86602263HCID 86602263, compound

Product 1

HCID 9958164HCID 9958164, compound

Conditions

Temperature
5 °C

Procedure

To a solution of the product obtained in Example 19 (210 mg) in THF (5 ml) were added 0.5N LiOH (1.54 ml) and 3% H2O2 (65 μl) at 5° C. The mixture was stirred at 5° C. for 14 hours and acidified with 1 N HCl. The mixture was concentrated, diluted with H2O and the resulting precipitate was collected by filtration and washed with H2O to yield the title compound (171 mg). mp. 182-184° C.; IR (Nujol) 3295, 1729, 1711, 1653 cm−1; MS (ESI) m/z 514 (M−H)

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with H2O

Sources & evidence

ORD record
ord-63fd96436db14f6299580a1137a5ca22
Source dataset
uspto-grants-2008_11
Patent number
US07456217B2

Reaction notes

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