Sodium hydrosulfide hydrate → HCID 178470127, compound

HRID 1096523Notes

Reaction equation

HRID 1096523 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([O:27][CH:28]([F:30])[F:29])[C:11]([N:18]3[CH2:22][CH2:21][C@@H:20]([C:23]([NH2:26])([CH3:25])[CH3:24])[CH2:19]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:31]2[CH2:33][CH2:32]2)[C:7]=1[S:34](C)(=O)=O)=[O:5])[CH3:2].O.[SH-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([O:27][CH:28]([F:29])[F:30])[C:11]([N:18]3[CH2:22][CH2:21][C@@H:20]([C:23]([NH2:26])([CH3:25])[CH3:24])[CH2:19]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:31]2[CH2:33][CH2:32]2)[C:7]=1[SH:34])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 16211346Sodium hydrosulfide hydrateHCID 58420493HCID 58420493, compound

Product 1

HCID 178470127HCID 178470127, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 14 (1.6 g, 2.93 mmol) is dissolved in DMF (40 mL) under an atmosphere of argon. Sodium hydrosulfide hydrate crystals (Aldrich, 72.6% by titration, 330 mg, 5.88 mmol) are added to this solution. The resulting mixture is sparged slowly with argon for 30 min. The progress of the reaction is monitored by HPLC-MS, and judged to be complete (≧2% of 14 remains) after 5 h. Excess sodium hydrosulfide is quenched upon addition of aq. HCl (4.5 mL, 4 N). The resulting orange solution (pH ˜2) is sparged with argon (30 min) to remove the generated hydrogen sulfide. DMF is removed under reduced pressure to give orange oil.

Workup

  1. customThe resulting mixture is sparged slowly with argon for 30 min
  2. customafter 5 h
  3. customExcess sodium hydrosulfide is quenched upon addition of aq. HCl (4.5 mL, 4 N)
  4. customThe resulting orange solution (pH ˜2) is sparged with argon (30 min)
  5. customto remove the generated hydrogen sulfide
  6. customDMF is removed under reduced pressure
  7. customto give orange oil

Sources & evidence

ORD record
ord-df805fb8af794f22ad89d7a66a919d92
Source dataset
uspto-grants-2012_03
Patent number
US08138346B2

Reaction notes

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