Acetic Acid → HCID 86742942, compound

HRID 620783Notes

Reaction equation

HRID 620783 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21]([NH2:23])=[O:22])[CH2:6]1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO.C(OCC)(=O)C>[CH2:13]([O:12][C:10]([N:8]1[CH2:9][C@@H:5]([SH:4])[CH2:6][C@H:7]1[CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21]([NH2:23])=[O:22])=[O:11])[CH:14]=[CH2:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 54244021HCID 54244021, compound

Product 1

HCID 86742942HCID 86742942, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (8.20 g) in methanol (82 ml) was added sodium methoxide (28% solution in methanol) (5.7 ml) at -10°-0° C. in a nitrogen stream and the mixture was stirred at the same condition for 1 hour. To the mixture was added glacial acetic acid (1.9 ml) at -10°-0° C. The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate (100 ml). The solution was washed with water (100 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (75 g) and eluted with a mixture of methanol and chloroform (2:98 V/V) to give (2S,4S)-1-allyloxycarbonyl-4-mercapto-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (6.89 g)

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a residue
  3. washThe solution was washed with water (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with a mixture of methanol and chloroform (2:98 V/V)

Sources & evidence

ORD record
ord-a5630290d508419fb7b6a8afc9baf9b0
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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