Hydrochloric Acid → HCID 14830224, compound

HRID 1088288Notes

Reaction equation

HRID 1088288 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(=O)C)[CH2:14][C@H:13]2[CH2:21][CH2:22][O:23]C(=O)C)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>CO.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([SH:17])[CH2:14][C@H:13]2[CH2:21][CH2:22][OH:23])=[O:11])=[CH:27][CH:28]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15671532HCID 15671532, compound

Product 1

HCID 14830224HCID 14830224, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2R,4S)-1-p-Nitrobenzyloxycarbonyl-2-(2-acetoxyethyl)-4-acetylthiopyrrolidine (204 mg) was dissolved in 5 ml of methanol and 1 ml of 1N sodium hydroxide solution was added thereto at room temperature under nitrogen stream, followed by stirring for 30 minutes. 1H Hydrochloric acid (1.2 ml) was added to the reaction mixture. The resulting mixture was diluted with ethyl acetate, washed with brine five times, dried over anhydrous sodium sulfate and evaporated to give an oily residue, which was purified by silica gel thin layer chromatogaraphy to give (2R,4S)-1-p-nitrobenzyloxycarbonyl-2-(2-hydroxyethyl)-4-mercaptopyrrolidine.

Workup

  1. customat room temperature
  2. washwashed with brine five times
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give an oily residue, which
  6. customwas purified by silica gel thin layer chromatogaraphy

Sources & evidence

ORD record
ord-1d4b05a739844d1f8a3fbbfceac9fa60
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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