Hexane → HCID 57704765, compound

HRID 2093203Notes

Reaction equation

HRID 2093203 reaction equation
[F:1][C:2]([F:51])([F:50])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([I:30])[C:21]=3[C:31]3[CH:32]=[C:33]([C:38]4[CH:43]=[CH:42][C:41]([C:44]([O:46]C)=[O:45])=[CH:40][C:39]=4[CH3:48])[CH:34]=[CH:35][C:36]=3[Cl:37])[C@H:14]2[CH3:49])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O[Li].O.CCOC(C)=O.CCCCCC>O1CCOCC1>[F:51][C:2]([F:1])([F:50])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[C:22]([I:30])[C:21]=3[C:31]3[CH:32]=[C:33]([C:38]4[CH:43]=[CH:42][C:41]([C:44]([OH:46])=[O:45])=[CH:40][C:39]=4[CH3:48])[CH:34]=[CH:35][C:36]=3[Cl:37])[C@H:14]2[CH3:49])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 57704776HCID 57704776, compound

Product 1

HCID 57704765HCID 57704765, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the title compound from Step B (30 mg, 0.035 mmol) in dioxane (2 ml) at room temperature, an aqueous solution of LiOH.H2O (7.36 mg, 0.175 mmol) was added. The mixture was stirred at room temperature for overnight. TLC (EtOAc:hexane/2:8) showed no starting material. The solvent was removed. 1N HCl (1 ml) was added. The mixture was extracted with methylene chloride (3×10 ml). The combined methylene chloride layers were dried over sodium sulfate. The title compound was obtained by preparative reverse phase HPLC as a colorless solid.

Workup

  1. customThe solvent was removed
  2. addition1N HCl (1 ml) was added
  3. extractionThe mixture was extracted with methylene chloride (3×10 ml)
  4. dry with materialThe combined methylene chloride layers were dried over sodium sulfate

Sources & evidence

ORD record
ord-dc40655e390d46c293d9f00ea9b8f65a
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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