HCID 58092758, compound → HCID 66851478, compound

HRID 1807680Notes

Reaction equation

HRID 1807680 reaction equation
[C:1]([OH:4])(=S)[CH3:2].[N:5]([CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C@@H:10]1[C:22]([NH2:24])=[O:23])=[N+]=[N-]>CCOCC>[C:1]([NH:5][CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C@@H:10]1[C:22]([NH2:24])=[O:23])(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 58092758HCID 58092758, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 66851478HCID 66851478, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thioacetic acid (2.312 mmol) was added to (2S,3S)-3-azidomethyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid amide (Stage 36.3) (0.578 mmol) at rt with the formation of nitrogen gas. After stirring for 16 h, the reaction mixture was diluted with Et2O, the solids were removed by filtration and the filtrate was concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a light yellow oil (thiol odor). HPLC: tR=3.71 min (method H); LC-MS: tR=0.64 min, [M+H]+ 290 (method I); TLC: Rf=0.38 (200:20:1 CH2Cl2/MeOH/conc. NH4OH).

Workup

  1. customthe solids were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3df0234b55954fae9ed545cbb3289ede
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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