Methanol → HCID 53808805, compound

HRID 2226579Notes

Reaction equation

HRID 2226579 reaction equation
[Na].Br[C@H:3]([CH2:7]O)[C:4]([OH:6])=[O:5].[CH3:9][CH:10]([SH:12])[CH3:11].C[OH:14]>C[O-].[Na+]>[OH:14][C@@H:3]([CH2:7][S:12][CH:10]([CH3:11])[CH3:9])[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 887Methanol3×HCID 63642-PropanethiolHCID 5360545Sodium2×HCID 13776211110994-91-7

Product 1

HCID 53808805HCID 53808805, compound

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Sodium (7.09 g, 308 mmol) in methanol (100 ml) was added over 35 min to a stirred solution of (R)-2-bromo-3-hydroxypropanoic acid (25.5 g, 151 mmol) in methanol (200 ml) at -25°. The temperature was allowed to reach 10° and the mixture stirred for a further 2 h. 2-Propanethiol (11.4 ml, 240 mmol) in sodium methoxide solution, prepared from sodium (5.68 g, 247 mmol) and methanol (100 ml) was added to this suspension (240 ml, 120 mmol) at -5°. After 16 h at room temperature the solvent was evaporated and the residue dissolved in water/ether/conc. hydrochloric acid to a final pH of approximately 1. The organic phase was separated and the aqueous phase re-extracted with ether (×2). The combined organic extracts were dried (Na2SO4) and the solvent evaporated to give the sub-title compound (18.56 g).

Workup

  1. customto reach 10°
  2. customAfter 16 h at room temperature the solvent was evaporated
  3. dissolutionthe residue dissolved in water/ether/conc
  4. customThe organic phase was separated
  5. extractionthe aqueous phase re-extracted with ether (×2)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-652d874fbcc741c289d364cfd597c67c
Source dataset
uspto-grants-1994_09
Patent number
US05348978

Reaction notes

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