Hexane → HCID 57704773, compound

HRID 607078Notes

Reaction equation

HRID 607078 reaction equation
[F:1][C:2]([F:52])([F:51])[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:39]4[CH:44]=[CH:43][C:42]([C:45]([O:47]C)=[O:46])=[CH:41][C:40]=4[CH3:49])[CH:34]=[CH:35][C:36]=3[O:37][CH3:38])[C@H:14]2[CH3:50])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O[Li].O.CCOC(C)=O.CCCCCC>O1CCOCC1>[F:52][C:2]([F:1])([F:51])[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:39]4[CH:44]=[CH:43][C:42]([C:45]([OH:47])=[O:46])=[CH:41][C:40]=4[CH3:49])[CH:34]=[CH:35][C:36]=3[O:37][CH3:38])[C@H:14]2[CH3:50])[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 57704811HCID 57704811, compound

Product 1

HCID 57704773HCID 57704773, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the title compound from Step G (0.016 g, 0.0188 mmol) in dioxane (2 ml) at room temperature, an aqueous solution of LiOH.H2O (0.007 g, 0.16 mmol) (1 ml) was added. The mixture was stirred at room temperature for 5 h. TLC (EtOAc:hexane/2:8) showed no starting material. The solvent was removed. 1N HCl (1 ml) was added. The mixture was extracted with EtOAc (3×15 ml). The combined EtOAc layers were dried over sodium sulfate. The title compound was obtained by preparative reverse phase HPLC. 1H NMR (CDCl3, 500 MHz): δ2:1 mixture of atropisomers 8.21 (s, 1H), 8.01 (s, 1H), 7.94 (d, J=7.5 Hz, 1H), 7.89 (s, 1H), 7.72 (s, 1H), 7.69 (s, 1H), 7.66 (d, J=7.5 Hz, 1H), 7.45 (m, 1H), 7.37 (m, 1H), 7.14 (m, 1H), 7.00 (m, 1H), 5.60 (d, J=8 Hz, 0.66H), 5.54 (d, J=8 Hz, 0.33H), 4.82 (d, J=7.5 Hz, 0.33H), 4.79 (d, J=8 Hz, 0.66H), 3.99 (d, J=10 Hz, 0.33H), 3.96 (d, J=9.5 Hz, 0.66H), 3.91 (m, 1H), 3.90 (s, 2H), 3.86 (s, 1H), 2.42 (s, 1H), 2.41 (s, 2H), 0.60 (d, J=7 Hz, 1H), 0.55 (d, J=6.5 Hz, 2H).

Workup

  1. customThe solvent was removed
  2. addition1N HCl (1 ml) was added
  3. extractionThe mixture was extracted with EtOAc (3×15 ml)
  4. dry with materialThe combined EtOAc layers were dried over sodium sulfate

Sources & evidence

ORD record
ord-a181ef4c1efb4cdcaee6b47473361c49
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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