Pyridine → HCID 131726118, compound

HRID 724553Notes

Reaction equation

HRID 724553 reaction equation
C[O:2][C:3](=[O:63])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:29][CH2:30][N:31]([C:33]4[CH:38]=[CH:37][C:36]([C@H:39]5[CH2:56][C@@:54]6([CH3:55])[C@@H:50]([CH2:51][CH2:52][C@:53]6([OH:60])[C:57]#[C:58][CH3:59])[C@H:49]6[C:40]5=[C:41]5[C:46]([CH2:47][CH2:48]6)=[CH:45][C:44](=[O:61])[CH2:43][CH2:42]5)=[CH:35][CH:34]=4)[CH3:32])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:62])[CH2:10][CH2:9]1)[CH3:7].[CH3:64][S:65][CH2:66]Cl.N1C=CC=C[CH:69]=1>>[CH3:69][CH:4]([CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:29][CH2:30][N:31]([C:33]4[CH:34]=[CH:35][C:36]([C@H:39]5[CH2:56][C@@:54]6([CH3:55])[C@@H:50]([CH2:51][CH2:52][C@:53]6([OH:60])[C:57]#[C:58][CH3:59])[C@H:49]6[C:40]5=[C:41]5[C:46]([CH2:47][CH2:48]6)=[CH:45][C:44](=[O:61])[CH2:43][CH2:42]5)=[CH:37][CH:38]=4)[CH3:32])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[O:62][CH2:64][S:65][CH3:66])[CH2:10][CH2:9]1)[CH3:7])[C:3]([OH:2])=[O:63]

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-dd59505439b54a67842fc20d6bb42556
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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