Thioglycolic Acid → HCID 67350930, compound

HRID 1672850Notes

Reaction equation

HRID 1672850 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:15]([C:22](OCC)=O)=[N:16][C:17](OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:46]1[CH2:56][CH2:55][N:54]2[C:49](=NCCC2)[CH2:48][CH2:47]1.SC[C:59]([OH:61])=[O:60]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:54][C:49]1[CH:48]=[CH:47][CH:46]=[C:56]([C:22]2[O:61][C:59](=[O:60])[N:16]([CH3:17])[N:15]=2)[CH:55]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 5

HCID 1133Thioglycolic AcidHCID 11776TriphenylphosphineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 67350930HCID 67350930, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

N-[3-(4-Methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)phenyl]-2-nitrobenzenesulfoneamide (2.50 g, 6.64 mmol) obtained in Step 4 was dissolved in toluene (13 mL), and the mixture was stirred at 60° C. for 5 hours after adding commercially available (S)-(−)-1-tert-butoxycarbonyl-2-pyrrolidinemethanol (2.67 g, 13.3 mmol), diethyl azodicarboxylate (40% toluene solution, 6.1 mL, 13.3 mmol), and triphenylphosphine (3.49 g, 13.3 mmol). Water and ethyl acetate were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain a crude purified product. The crude purified product was dissolved in DMF (33 mL), and the mixture was stirred for 3 hours after adding DBU (3.98 mL, 26.7 mmol) and mercaptoacetic acid (0.92 mL, 13.3 mmol). Water and ethyl acetate were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (S)-1-tert-butoxycarbonyl-2-{N-[3-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)phenyl]aminomethyl}pyrrolidine (1.37 g, 55%).

Workup

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography
  5. customto obtain a crude
  6. custompurified product
  7. customThe crude purified product
  8. dissolutionwas dissolved in DMF (33 mL)
  9. stirringthe mixture was stirred for 3 hours
  10. customto separate the organic layer
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bcdd55dddcd349cea46c01c9207f905e
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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