Hydrogen Sulfide → HCID 44305151, compound

HRID 1656042Notes

Reaction equation

HRID 1656042 reaction equation
C([S:5][CH2:6][C:7]1([C:16]([NH:18][CH2:19][C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[O:17])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)(C)(C)C.C1(OC)C=CC=CC=1.S>FC(F)(F)C(O)=O>[SH:5][CH2:6][C:7]1([C:16]([NH:18][CH2:19][C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[O:17])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 7519AnisoleHCID 131718215HCID 131718215, compound

Product 1

HCID 44305151HCID 44305151, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve N-[[2-[[(t-butyl)thio]methyl]-2,3-dihydro-1H-indene-2-yl]carbonyl]-glycine, benzyl ester (262 mg, 0.64 mmol) in trifluoroacetic acid (3 mL) and add excess anisole followed by mercuric acetate (203 mg, 0.64 mmol). Stir at room temperature for 18 hours then treat with gaseous hydrogen sulfide. Partition the mixture between methylene chloride/water (150 mL). Separate the organic phase and wash with dilute brine. Dry (MgSO4) and evaporate the solvent in vacuo to give a clear oil. Purify by silica gel chromatography (30% ethyl acetate/hexane) to give the title compound as a crystalline solid (213 mg, 94%); mp 92°-93° C. (methylene chloride/hexane).

Workup

  1. customPartition the mixture between methylene chloride/water (150 mL)
  2. customSeparate the organic phase
  3. washwash with dilute brine
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customto give a clear oil
  7. customPurify by silica gel chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-94127ba5e28245259cacb6de200f55b5
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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