Hydrochloric Acid → HCID 56617601, compound

HRID 1088263Notes

Reaction equation

HRID 1088263 reaction equation
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17]C(=O)C3C=CC=CC=3)[CH2:14][C@H:13]2[CH2:26][NH:27][C:28]([NH:30]C(=O)C(Cl)(Cl)Cl)=[O:29])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>CO>[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]([OH:17])[CH2:14][C@H:13]2[CH2:26][NH:27][C:28]([NH2:30])=[O:29])=[O:11])=[CH:37][CH:38]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15671459HCID 15671459, compound

Product 1

HCID 56617601HCID 56617601, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-trichloroacetylaminocarbonylaminomethyl-4-benzoyloxypyrrolidine (431 mg) was dissolved in 10 ml of methanol, and 1.48 ml of 1N sodium hydroxide solution was added thereto, followed by stirring at room temperature for 1.5 hours. 1N Hydrochloric acid (1.48 ml) was added thereto, followed by concentration to remove methanol. The residue was diluted with methylene chloride, washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel thin layer chromatography to obtain (2S,4R)-1-(p-nitrobenzyloxycarbonyl)-2-aminocarbonylaminomethyl-4-hydroxypyrrolidine.

Workup

  1. concentrationfollowed by concentration
  2. customto remove methanol
  3. additionThe residue was diluted with methylene chloride
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-e8401ae5197945649b5267dcf820d595
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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