Hydrochloric Acid → HCID 69315002, compound

HRID 1391713Notes

Reaction equation

HRID 1391713 reaction equation
[Li+].[OH-].O.[C:4]([NH:7][C@:8]1([CH:22]([CH2:24][CH3:25])[CH3:23])[CH2:12][CH2:11][N:10]([C@@H:13]([CH2:18][CH:19]=[CH2:20])[C:14]([O:16]C)=[O:15])[C:9]1=[O:21])(=[O:6])[CH3:5].Cl>C1COCC1>[C:4]([NH:7][C@:8]1([CH:22]([CH2:24][CH3:25])[CH3:23])[CH2:12][CH2:11][N:10]([C@@H:13]([CH2:18][CH:19]=[CH2:20])[C:14]([OH:16])=[O:15])[C:9]1=[O:21])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69316592(s)-Methyl 2-((s)-3-acetamido-3-sec-butyl-2-oxopyrrolidin-1-yl)pent-4-enoate

Product 1

HCID 69315002HCID 69315002, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step L (7): A solution of LiOH/H2O (2M, 28 mg in 0.50 mL) was added to the diastereomer B, (S)-methyl 2-((S)-3-acetamido-3-sec-butyl-2-oxopyrrolidin-1-yl)pent-4-enoate (122 mg, 0.39 mmol) from Step L (6) in THF (1.0 mL) at RT. The reaction was stirred for 3 days. The mixture was poured into 1N HCl and the aqueous layer was extracted with EtOAC. The combined organic layers were washed with brine, dried over NaSO4 and concentrated in vacuo to give 102 mg of the title compound as white solid. LC-MS (M+H)+=297.01.

Workup

  1. extractionthe aqueous layer was extracted with EtOAC
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over NaSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99cbc239ed154870975f576a4d3ff0b8
Source dataset
uspto-grants-2008_03
Patent number
US07338974B2

Reaction notes

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