Acetic Acid → HCID 57228158, compound

HRID 703579Notes

Reaction equation

HRID 703579 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][O:24][CH2:25][C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])[CH2:6]1)(=O)C.[H-].[Na+].C(O)(=O)C>C(O)C=C.C(OCC)(=O)C>[CH2:29]([O:28][C:26]([CH2:25][O:24][CH2:23][C@@H:7]1[CH2:6][C@H:5]([SH:4])[CH2:9][N:8]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11])=[O:27])[CH:30]=[CH2:31]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 57063209(2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 57228158HCID 57228158, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 7858Allyl AlcoholSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-4-acetylthio- 2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (4.25 g) in allyl alcohol (40 ml) was added sodium hydride (62.8% in oil suspension) (0.5 g) at -5°~0° C. in a nitrogen stream. After stirring for 1 hour, acetic acid (1 ml) was added to the mixture. The mixture was concentrated under reduced pressure to give a syrup. The syrup was dissolved in ethyl acetate (50 ml), washed in turn with water (50 ml) and brine (50 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 (30 g) and eluted with chloroform to give (2S,4S)-2-(allyloxycarbonylmethyloxymethyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.29 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a syrup
  3. washwashed in turn with water (50 ml) and brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-c24ec7255c0f4ce0a9f85bcf8a1d1f78
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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