Sodium hydrosulfide hydrate → HCID 178470125, compound

HRID 601461Notes

Reaction equation

HRID 601461 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([O:27][CH3:28])[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:29]2[CH2:31][CH2:30]2)[C:7]=1[S:32](C)(=O)=O)=[O:5])[CH3:2].O.[SH-].[Na+]>COCCOC.O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([O:27][CH3:28])[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:29]2[CH2:30][CH2:31]2)[C:7]=1[SH:32])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 16211346Sodium hydrosulfide hydrateHCID 58420505HCID 58420505, compound

Product 1

HCID 178470125HCID 178470125, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Compound 7 (1.04 g, 2.04 mmol) is partially dissolved in DME (40 mL) under an atmosphere of argon. Sodium hydrosulfide hydrate (Aldrich, 72.6% by titration, 465 mg, 6.02 mmol) in water (3.0 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 7 remains) after 11.5 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.

Workup

  1. customThe resulting mixture is sparged slowly with argon for 30 min
  2. customafter 11.5 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

Sources & evidence

ORD record
ord-9fe078d5057f4a798805ebf472cc0212
Source dataset
uspto-grants-2011_03
Patent number
US07902365B2

Reaction notes

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