Sodium sulfide monohydrate → HCID 71271685, compound

HRID 1770640Notes

Reaction equation

HRID 1770640 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10](OS(C)(=O)=O)[CH2:11][CH2:12]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[S-2:24].[Na+].[Na+]>CO>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][S:24]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 19906495Sodium sulfide monohydrateHCID 86725181HCID 86725181, compound

Product 1

HCID 71271685HCID 71271685, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of crude methanesulfonic acid 1-(tert-butoxycarbonylamino-methyl)-3-methanesulfonyloxy-propyl ester (1.24 g) in methanol (25 ml) was added sodium sulfide monohydrate (0.84 g). The reaction mixture was stirred at 40° C. for 3 hours. The methanol was partially removed by distillation. Water was added and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated. The residue was purified over silica gel (ethyl acetate/heptanes, from 1:4 to 1:1) to give thietan-2-ylmethyl-carbamic acid tert-butyl ester (0.15 g).

Workup

  1. customThe methanol was partially removed by distillation
  2. additionWater was added
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified over silica gel (ethyl acetate/heptanes, from 1:4 to 1:1)

Sources & evidence

ORD record
ord-0b09d8596b5741b6a733b6898fef28e4
Source dataset
uspto-grants-2016_02
Patent number
US09247740B2

Reaction notes

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