Sodium methanethiolate → HCID 67287391, compound

HRID 46197Notes

Reaction equation

HRID 46197 reaction equation
Cl[C:2]1[S:3][C:4]([CH2:7][C:8]2[CH:13]=[C:12]([C@H:14]3[C@H:19]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@@H:18]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@H:17]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C@@H:16]([CH2:44][O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[O:15]3)[CH:11]=[CH:10][C:9]=2[Cl:53])=[N:5][N:6]=1.[CH3:54][S-:55].[Na+]>O1CCCC1>[Cl:53][C:9]1[CH:10]=[CH:11][C:12]([C@H:14]2[C@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@@H:18]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C@H:17]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@@H:16]([CH2:44][O:45][CH2:46][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[O:15]2)=[CH:13][C:8]=1[CH2:7][C:4]1[S:3][C:2]([S:55][CH3:54])=[N:6][N:5]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 672869552-Chloro-5-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-1,3,4-thiadiazole

Product 1

HCID 67287391HCID 67287391, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-1,3,4-thiadiazole (419 mg, 0.55 mmol) from Step 2 in tetrahydrofuran (10 mL) was added sodium methanethiolate (77 mg, 1.1 mmol). The resulting mixture was stirred at ambient temperature overnight. After cooling to 0° C., the reaction was quenched with hydrochloric acid (1.0 M) and diluted with ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes) to yield the title compound (331 mg, 0.42 mmol, 77%) as a yellow oil. MH+ 779.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction was quenched with hydrochloric acid (1.0 M)
  3. additiondiluted with ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1b8032a7eb284b2a98884ad809915433
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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