Sodium hydrosulfide hydrate → HCID 178470126, compound

HRID 1096525Notes

Reaction equation

HRID 1096525 reaction equation
[NH2:1][C@H:2]([C@@H:4]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]([O:19][CH3:20])=[C:17]3[C:12]([C:13](=[O:33])[C:14]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:15]([S:24](C)(=O)=O)[N:16]3[CH:21]3[CH2:23][CH2:22]3)=[CH:11][C:10]=2[F:34])[CH2:5]1)[CH3:3].O.[SH-].[Na+]>COCCOC.O>[NH2:1][C@H:2]([C@@H:4]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]([O:19][CH3:20])=[C:17]3[C:12]([C:13](=[O:33])[C:14]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:15]([SH:24])[N:16]3[CH:21]3[CH2:22][CH2:23]3)=[CH:11][C:10]=2[F:34])[CH2:5]1)[CH3:3]

Participants

5

Reactant 2

HCID 16211346Sodium hydrosulfide hydrateHCID 58420498HCID 58420498, compound

Product 1

HCID 178470126HCID 178470126, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Compound 18 from previous reaction is partially dissolved in DME (150 mL) under an atmosphere of argon. Sodium hydrosulfide hydrate (Aldrich, 72.6% by titration, 4.65 g, 60.2 mmol) in water (15.0 mL) is 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 18 remains) after 15 h. Excess sodium hydrosulfide is quenched upon addition of aq HCl (30 mL, 6 N). The resulting orange solution (pH ˜2) is sparged with argon (3 h) to remove the generated hydrogen sulfide.

Workup

  1. customThe resulting mixture is sparged slowly with argon for 30 min
  2. customafter 15 h
  3. customExcess sodium hydrosulfide is quenched upon addition of aq HCl (30 mL, 6 N)
  4. customThe resulting orange solution (pH ˜2) is sparged with argon (3 h)
  5. customto remove the generated hydrogen sulfide

Sources & evidence

ORD record
ord-b2b8b8a9ba1648f9905e3a5a8fc8c093
Source dataset
uspto-grants-2012_03
Patent number
US08138346B2

Reaction notes

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