Lithium Hydroxide → HCID 57418667, compound

HRID 2354361Notes

Reaction equation

HRID 2354361 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:28])[C@:6]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)([CH3:15])[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>C1COCC1>[C:19]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:18]=[CH:17][C:16]([C@@:6]([C:5]([OH:28])=[O:4])([CH3:15])[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[O:9])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68454132HCID 68454132, compound

Product 1

HCID 57418667HCID 57418667, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1.63 ml, 1M) was added dropwise to a solution of methyl-N-Boc-2-(4-biphenylyl)alaninate (482 mg, 1.36 mmol) in THF (3 ml). The resulting mixture was stirred at rt for 16 h. Solvent was removed under reduced pressure and the residue was taken up in water (10 ml) and washed with EtOAc. The aqueous layer was acidified with HCl (1M) to pH ˜2 and the product was extracted by EtOAc (3×10 ml). The combined extracts were washed with water and brine, dried and concentrated which left 470 mg (90%) as a white solid. MS (ES) m/e 342.4 [M+H]+

Workup

  1. customSolvent was removed under reduced pressure
  2. washwashed with EtOAc
  3. extractionthe product was extracted by EtOAc (3×10 ml)
  4. washThe combined extracts were washed with water and brine
  5. customdried
  6. concentrationconcentrated which
  7. waitleft 470 mg (90%) as a white solid

Sources & evidence

ORD record
ord-b14e1d33cb2c4e6ebaaa20a89f88c848
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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