Hydrochloric Acid → (2S,4R)-2-(carbamoylmethyl)thiomethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1088952Notes

Reaction equation

HRID 1088952 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([CH2:27][S:28][CH2:29][C:30](=[O:32])[NH2:31])[CH2:10]1)(C(C)(C)C)(C)C.Cl>CO.C(OCC)(=O)C>[C:30]([CH2:29][S:28][CH2:27][C@@H:11]1[CH2:10][C@@H:9]([OH:8])[CH2:13][N:12]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)=[O:15])(=[O:32])[NH2:31]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57024589(2S,4R)-4-t-butyldimethylsilyloxy-2-(carbamoylmethyl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 10666767(2S,4R)-2-(carbamoylmethyl)thiomethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 67.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-4-t-butyldimethylsilyloxy-2-(carbamoylmethyl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.10 g) in methanol (40 ml) was added conc. hydrochloric acid (0.72 ml) at ambient temperature. After stirring at the same temperature for 1 hour, this reaction mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate (60 ml). The solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give a residue. The residue was washed with a mixture of ethyl acetate (30 ml) and diisopropyl ether (15 ml). The resulting precipitates were collected by filtration and air-dried to give (2S,4R)-2-(carbamoylmethyl)thiomethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.08 g).

Workup

  1. concentrationthis reaction mixture was concentrated under reduced pressure
  2. customto give a residue
  3. washThe solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customto give a residue
  7. washThe residue was washed with a mixture of ethyl acetate (30 ml) and diisopropyl ether (15 ml)
  8. customThe resulting precipitates
  9. filtrationwere collected by filtration
  10. customair-dried

Sources & evidence

ORD record
ord-b482ad3bcf964d2eae0fa61f7247f2b5
Source dataset
uspto-grants-1990_10
Patent number
US04963543

Reaction notes

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