Pyridine → HCID 131726118, compound

HRID 2112315Notes

Reaction equation

HRID 2112315 reaction equation
[OH:1][C@@H:2]1[CH2:26][C@H:25]2[C@:20]([CH3:61])([CH2:21][CH2:22][C@H:23]([O:27][CH2:28][CH2:29][N:30]([C:32]3[CH:37]=[CH:36][C:35]([C@H:38]4[CH2:55][C@@:53]5([CH3:54])[C@@H:49]([CH2:50][CH2:51][C@:52]5([OH:59])[C:56]#[C:57][CH3:58])[C@H:48]5[C:39]4=[C:40]4[C:45]([CH2:46][CH2:47]5)=[CH:44][C:43](=[O:60])[CH2:42][CH2:41]4)=[CH:34][CH:33]=3)[CH3:31])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:63])([C@@H:17]([OH:62])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13]C)=[O:12])[CH2:6][CH2:5]1.[CH3:64][S:65][CH2:66]Cl.N1C=CC=C[CH:69]=1>>[CH3:69][CH:10]([CH2:9][C@H:8]([C@@H:7]1[C@:16]2([CH3:63])[C@H:4]([C@H:3]3[C@H:19]([CH2:18][C@@H:17]2[OH:62])[C@:20]2([CH3:61])[C@@H:25]([CH2:24][C@@H:23]([O:27][CH2:28][CH2:29][N:30]([C:32]4[CH:33]=[CH:34][C:35]([C@H:38]5[CH2:55][C@@:53]6([CH3:54])[C@@H:49]([CH2:50][CH2:51][C@:52]6([OH:59])[C:56]#[C:57][CH3:58])[C@H:48]6[C:39]5=[C:40]5[C:45]([CH2:46][CH2:47]6)=[CH:44][C:43](=[O:60])[CH2:42][CH2:41]5)=[CH:36][CH:37]=4)[CH3:31])[CH2:22][CH2:21]2)[CH2:26][C@H:2]3[O:1][CH2:64][S:65][CH3:66])[CH2:5][CH2:6]1)[CH3:15])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 3

HCID 1049PyridineHCID 16916Chloromethyl methyl sulfideHCID 131726114HCID 131726114, compound

Product 1

HCID 131726118HCID 131726118, compound

Procedure

The compound of Example 1I is dissolved in pyridine and cooled in an ice bath; methylthiomethyl chloride (1.2 eq) is added, and the mixture is warmed to ambient temperature, then heated to 90° C. overnight. The solvents are removed in vacuo; the residue is partitioned between aqueous phosphoric acid (1N) and ethyl acetate. The organic extract is washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude material is purified by column chromatography.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureheated to 90° C. overnight
  3. customThe solvents are removed in vacuo
  4. customthe residue is partitioned between aqueous phosphoric acid (1N) and ethyl acetate
  5. extractionThe organic extract
  6. washis washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-a7e36f95b60c4753b25cc7c69414f4d8
Source dataset
uspto-grants-2009_04
Patent number
US07521439B2

Reaction notes

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