Ethanethiol → HCID 178477456, compound

HRID 1728482Notes

Reaction equation

HRID 1728482 reaction equation
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].C(O[CH:10]1[NH:13][C:12](=[O:14])[CH:11]1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])=[N:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])(=O)C>C1COCC1>[CH2:3]([S:5][C@@H:10]1[NH:13][C:12](=[O:14])[C@H:11]1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])=[N:20][C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[CH3:4]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 178475771HCID 178475771, compound

Product 1

HCID 178477456HCID 178477456, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a 0° C. suspension of NaH (60% oil dispersion, 200 mg, 498 mmol) in THF (20 ml) was added ethanethiol (0.37 mL, 4.98 mmol). The resultant mixture was stirred for 10 min, cooled to -20° C., and compound 13 (1.9 g, 3.83 mmol) was added. The solution was stirred further for 30 min at room temperature and concentrated. The residue was partitioned between ethyl acetate and pH 7.0 aqueous buffer. The organic phase was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (Et2O) to afford 718 mg (36%) of the title product.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and pH 7.0 aqueous buffer
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (Et2O)

Sources & evidence

ORD record
ord-d49824e5cde8457781b124465678a8c0
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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