Water → HCID 53642688, compound

HRID 1379638Notes

Reaction equation

HRID 1379638 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:10]([O:14][C:15]([NH:17][CH2:18][CH:19](O)C)=[O:16])([CH3:13])([CH3:12])[CH3:11].O.[CH2:23]1COCC1>>[C:10]([O:14][C:15]([NH:17][C@H:18]([CH3:19])[CH2:23][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:16])([CH3:11])([CH3:12])[CH3:13]

Participants

6

Reactant 5

HCID 962WaterHCID 7969ThiophenolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 9920508tert-butyl N-(2-hydroxypropyl)carbamate

Product 1

HCID 53642688HCID 53642688, compoundYield 85%

Procedure

Thiophenol (1.5 g, 14 mmol) was dissolved in dry THF (100 ml) and a 60% oil dispersion of sodium hydride (0.30 g, 14 mmol) was added in portions under nitrogen. After stirring for 15 min. at room temperature, the mesylate ester of N-tert-butoxycarbonyl-2-hydroxypropylamine (3.2 g, 14 mmol) was added in three portions and the reaction mixture was heated at 70° C. for 18 h. After cooling, water (30 ml) was added, the aqueous phase was separated and washed with dichloromethane (50 ml). The combined organic phases were dried (MgSO4) and evaporated to give (R)- N-tertbutyloxycarbonyl-1-phenylthio-2-propylamine as a fawn oil (3.2 g, 85%), TLC Rf 0.64 [SiO2 : heptanethyl acetate (1:1)].

Workup

  1. temperaturethe reaction mixture was heated at 70° C. for 18 h
  2. temperatureAfter cooling
  3. customthe aqueous phase was separated
  4. washwashed with dichloromethane (50 ml)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-eaa034b37e494dd782aa84b479bc738f
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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