Lithium Hydroxide → HCID 6915692, compound

HRID 2222970Notes

Reaction equation

HRID 2222970 reaction equation
C([O:3][C:4](=[O:24])[CH:5]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)C.[OH-].[Li+]>O1CCCC1>[C:20]([O:19][C:17]([NH:16][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[C:4]([OH:24])=[O:3])=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68803174HCID 68803174, compound

Product 1

HCID 6915692HCID 6915692, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 2-tert-butoxycarbonylamino-3-(3-nitro-phenyl)-propionic acid ethyl ester (1.00 g , ≈2.96 mmol) in tetrahydrofuran (10 mL) was added 3M aqueous lithium hydroxide solution (3 mL, 9 mmol) and the mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated to dryness, the residue taken up in water (20 mL) and extracted with ether (2×10 mL). The aqueous layer was filtered through Celite®, cooled in ice and adjusted to pH=2 with 0.1M aqueous hydrochloric acid. The mixture was then extracted with dichloromethane (3×15 mL), dried over sodium sulfate and concetrated in vacuo to give crude 2-tert-butoxycarbonylamino-3-(3-nitro-phenyl)-propionic acid as a pale yellow solid which was used without further purification (0.63 g, ≈69%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionextracted with ether (2×10 mL)
  3. filtrationThe aqueous layer was filtered through Celite®
  4. temperaturecooled in ice
  5. extractionThe mixture was then extracted with dichloromethane (3×15 mL)
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-3a55285e7c1149b580b674ec7bc427b8
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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