Lithium Hydroxide → HCID 58691191, compound

HRID 1392097Notes

Reaction equation

HRID 1392097 reaction equation
[OH:1][C@@H:2]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:3]([NH:5][C@H:6]([C:11]([O:13]C)=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].[Li+].[OH-]>C1COCC1.Cl>[OH:1][C@@H:2]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:3]([NH:5][C@H:6]([C:11]([OH:13])=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 14776361HCID 14776361, compound

Product 1

HCID 58691191HCID 58691191, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl N-[(2S)-2-hydroxy-4-methylpentanoyl]-L-leucinate (7a) (2.13 g) dissolved in THF (21 mL) was added an aqueous 2.3 M LiOH solution (17 mL). The reaction mixture was stirred for 2 hours at room temperature, diluted with 1.2 N HCl (100 mL) and extracted with EtOAc. The organic layer was washed with brine and concentrated to give the desired product (1.75 g, 87%). 1H NMR (300 MHz, CDCl3) δ 0.92-0.96 (m, 12H), 1.50-1.71 (m, 5H), 1.82-1.90 (m, 1H), 4.17-4.22 (m, 1H), 4.50-4.57 (m, 1H), 7.26 (d, 1H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-59d6c4f5919744f39920c545c2efdce1
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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