Hydrochloric Acid → HCID 59423758, compound

HRID 501666Notes

Reaction equation

HRID 501666 reaction equation
[Li+].[OH-].O.[CH3:4][N:5]([C@@H:15]([CH2:20][CH:21]=[CH2:22])[C:16]([O:18]C)=[O:17])[C:6](=[O:14])[CH:7]([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10].Cl>C1COCC1>[CH3:4][N:5]([C@@H:15]([CH2:20][CH:21]=[CH2:22])[C:16]([OH:18])=[O:17])[C:6](=[O:14])[CH:7]([CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86622307HCID 86622307, compound

Product 1

HCID 59423758HCID 59423758, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step A (3): A solution of LiOH/H2O (2 M, 1.2 mL) was added to (S)-methyl 2-(N-methyl-2-propylpentanamido)pent-4-enoate (230 mg, 0.85 mmol) from Step A (2) in THF (4.0 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 206 mg (95% yield) of the title compound as a white solid. LC-MS (M+H)+=256.23. 1H NMR (300 MHz, CDCl3) δ 0.78-0.92 (m, 6H) 1.11-1.44 (m, 7H) 1.50-1.69 (m, 2H) 2.47-2.83 (m, 3H) 2.97 (s, 3H) 4.98-5.16 (m, 3H) 5.59-5.78 (m, 1H).

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-320167f3cfb942c1af025fc1d258faf1
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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