Hydrochloric Acid → HCID 15895102, compound

HRID 1953046Notes

Reaction equation

HRID 1953046 reaction equation
Cl.C(OC([N:9]1[C@@H:13]([C:14](=[O:24])[NH:15][O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12][C@@H:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:10]1=[O:33])=O)(C)(C)C.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[CH2:17]([O:16][NH:15][C:14]([C@H:13]1[CH2:12][C@@H:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:10](=[O:33])[NH:9]1)=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 8857Ethyl Acetate2×HCID 15895101HCID 15895101, compound

Product 1

HCID 15895102HCID 15895102, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas was bubbled for 3 minutes through a solution of (3S, 5R)-5-benzyloxycarbamoyl-3-(4-methoxyphenyl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester (270 mg, 0.61 mmol) in methylene chloride (40 mL). After stirring for an additional 10 minutes, the solvent was evaporated to leave a white foam. The title compound (169 mg, 80%) was isolated by flash chromatography (eluting with ethyl acetate) and recrystallization from a mixture of ethyl acetate and hexane.

Workup

  1. customthe solvent was evaporated
  2. customto leave a white foam

Sources & evidence

ORD record
ord-a1b95408a95a4206bd51a20614f5ccbb
Source dataset
uspto-grants-2000_09
Patent number
US06114361

Reaction notes

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