Lithium hydroxide, monohydrate → L-Valine, 3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-

HRID 659823Notes

Reaction equation

HRID 659823 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C@@H:3]([C:16]([O:18]C)=[O:17])[NH:4][C:5]([O:7][C@@H:8]1[CH2:10][C@H:9]1[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])=[O:6].O[Li].O>CO.O>[CH3:1][C:2]([CH3:21])([CH3:20])[C@@H:3]([C:16]([OH:18])=[O:17])[NH:4][C:5]([O:7][C@@H:8]1[CH2:10][C@H:9]1[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])=[O:6]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59287267L-Valine,3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-,methyl ester

Product 1

HCID 59287076L-Valine, 3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-Yield 98%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

A solution (0.1 M) of methyl 3-methyl-N-({[(1R,2R)-2-pent-4-en-1-ylcyclopropyl]oxy}carbonyl)-L-valinate in 2:1 mixture of MeOH/H2O was treated with LiOH.H2O (4 eq) and then heated at 60° C. for 4 h. The mixture was cooled and concentrated to half volume, then diluted with EtOAc and acidified with aqueous HCl (1 N). The organic layer was separated and washed with brine then dried. Removal of the volatiles afforded the title compound (98%) as an oil. MS (ES+) m/z 284 (M+H)+

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to half volume
  3. additiondiluted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customthen dried
  7. customRemoval of the volatiles

Sources & evidence

ORD record
ord-ca269026d3d5484fa82d96005a14e377
Source dataset
uspto-grants-2011_12
Patent number
US08080654B2

Reaction notes

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