Lithium Hydroxide → HCID 69950176, compound

HRID 843397Notes

Reaction equation

HRID 843397 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CO>[C:1]([O:5][C:6]([CH2:8][CH:9]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:19]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 131723198HCID 131723198, compound2×

Product 1

HCID 69950176HCID 69950176, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (R/S)-α-t-butoxycarbonylmethyl-4-benzyloxyphenylacetate (5.92 g, 16 mmol) 48a in MeOH (50 mL) was treated with 1 N LiOH (32 mL) for 3 hours and MeOH was removed by concentration in vacuo. EtOAc was added and the solution was acidified with citric acid to pH 3. The organic layer was separated and the water solution was extracted with EtOAc one more time. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to afford the acid (4.8 g, 84%) as a solid. MS (CI—NH3): (M+H)+=357.

Workup

  1. customMeOH was removed by concentration in vacuo
  2. additionEtOAc was added
  3. customThe organic layer was separated
  4. extractionthe water solution was extracted with EtOAc one more time
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cead759310dd4dab930bcc51122c51b1
Source dataset
uspto-grants-2002_04
Patent number
US06376665B1

Reaction notes

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