Sodium Sulfide → tert-Butyl thietan-3-ylcarbamate

HRID 660128Notes

Reaction equation

HRID 660128 reaction equation
S(O[CH2:6][CH:7]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:8]OS(=O)(=O)C)(=O)(=O)C.[S-2:22].[Na+].[Na+]>C(O)C>[C:18]([O:17][C:15]([NH:14][CH:7]1[CH2:8][S:22][CH2:6]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 108933932-[(tert-Butoxycarbonyl)amino]propane-1,3-diyl dimethanesulfonate

Product 1

HCID 57415771tert-Butyl thietan-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N-(tert-butyloxycarbonyl)-2-amino-1,3-propanediol dimesylate [prepared according to E. Benoist et al., Synthesis 1998, (8), 1113-1118] (25 g, 72.0 mmol) in ethanol (375 ml) is treated with sodium sulfide (Na2S.xH2O 32-38%, 16.82 g, ˜75.4 mmol) and the mixture is stirred at a temperature of 50° C. (bath 60° C.) for 45 minutes. The cooled reaction mixture is concentrated under reduced pressure and the solid residue poured into water, extracted with Et2O, the combined organic layers washed with brine, dried (Na2SO4), filtered, and concentrated. The crude solid product (12.6 g, 92%) is used in the next step without further purification.

Workup

  1. customThe cooled reaction mixture
  2. concentrationis concentrated under reduced pressure
  3. additionthe solid residue poured into water
  4. extractionextracted with Et2O
  5. washthe combined organic layers washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude solid product (12.6 g, 92%) is used in the next step without further purification

Sources & evidence

ORD record
ord-c59cf31467f74cdaa41619d56ca6a805
Source dataset
uspto-grants-2011_12
Patent number
US08084474B2

Reaction notes

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