Thioglycolic Acid → HCID 178447680, compound

HRID 1373502Notes

Reaction equation

HRID 1373502 reaction equation
CS(O[CH2:6][CH:7]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH3:8])(=O)=O.C(O)(=O)C[SH:22].[O-:25][CH2:26][CH3:27].[Na+]>C(O)C>[CH2:13]([O:12][C:10]([NH:9][CH:7]([CH3:8])[CH2:6][CH2:27][C:26]([OH:25])=[S:22])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 2723922Sodium ethoxideHCID 135930942-(Benzyloxycarbonylamino)propyl methanesulfonate

Product 1

HCID 178447680HCID 178447680, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In ethanol (120 ml) was dissolved 34.9 g (120 mmol) of 2-(benzyloxycarbonylamino)propyl methanesulfonate, followed by adding dropwise thereto a thiolate separately prepared from 14.42 g (120 mmol) of thioglycolic acid and a solution of sodium ethoxide (120 mmol) in ethanol. The reaction was carried out at room temperature for 30 minutes and then at 50° C. for 2 hours, after which the solvent was distilled off and water was added to the residue, followed by three runs of extraction with ethyl acetate. The extract solution was washed with saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 34.5 g (yield 92%) of 2-(benzyloxycarbonylamino)propylthioacetic acid.

Workup

  1. additionby adding dropwise
  2. waitat 50° C. for 2 hours
  3. distillationafter which the solvent was distilled off
  4. additionwater was added to the residue
  5. extractionfollowed by three runs of extraction with ethyl acetate
  6. washThe extract solution was washed with saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialsaturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-87386f78be8444cd9d09926b465c177c
Source dataset
uspto-grants-2007_01
Patent number
US07161032B2

Reaction notes

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