Hydrochloric Acid → HCID 57780934, compound

HRID 1011230Notes

Reaction equation

HRID 1011230 reaction equation
C([O:3][C:4](=[O:47])[CH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[C:21]([O:22][CH3:23])=[C:20]3[C:15]([C:16](=[O:45])[C:17]([C:29]([NH:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][C:34]=4[CH3:44])=[O:30])=[CH:18][N:19]3[CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:14][C:13]=2[F:46])[CH2:7]1)C.O1CCOCC1.[Li+].[OH-].Cl>C(OCC)(=O)C>[F:46][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([O:22][CH3:23])[C:12]=1[N:8]1[CH2:9][CH2:10][CH2:11][C@H:6]([CH2:5][C:4]([OH:47])=[O:3])[CH2:7]1)[N:19]([CH2:24][C:25]([F:28])([F:26])[F:27])[CH:18]=[C:17]([C:29]([NH:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]([F:41])([F:42])[F:43])=[CH:35][C:34]=1[CH3:44])=[O:30])[C:16]2=[O:45]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 57780961HCID 57780961, compound

Product 1

HCID 57780934HCID 57780934, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

83 mg (0.123 mmol) of the compound of Example 21 are stirred with 3.0 ml of dioxane and 614 μl of LiOH (1M solution in water, 5 eq.) at RT overnight. The mixture is acidified with 1N HCl and diluted with ethyl acetate. It is extracted by shaking twice with water and once with a saturated NaCl solution. The organic phase is dried over magnesium sulfate and freed from the solvent on a rotary evaporator. The residue is dried under HV. 73 mg of the title compound (90% of theory) are obtained.

Workup

  1. extractionIt is extracted
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customfreed from the solvent on a rotary evaporator
  4. customThe residue is dried under HV

Sources & evidence

ORD record
ord-4a99fb44d58c454294ff86b7f9a27cd9
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

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