Lithium Hydroxide → [4-(2-Boc-amino-ethyl)-phenyl]-acetic acid

HRID 484450Notes

Reaction equation

HRID 484450 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 19747487HCID 19747487, compound

Product 1

HCID 19747634[4-(2-Boc-amino-ethyl)-phenyl]-acetic acidYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(tertiarybutyloxy carbonylaminoethyl)-phenylacetate (0.500 g, 1.71 mmol) in a mixture of tetrahydrofuran (20 ml) and water (10 ml) was added aqueous lithium hydroxide (3.8 ml of a 0.50M solution, 1.90 mmol) and the resulting mixture was stirred at room temperature for 16 h. The organic solvent was removed under vacuum and the residue was diluted with water (40 ml), acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with brine (1×30 ml), dried (MgSO4) and evaporated to give the pure title compound as colourless crystals (0.460 g), m.p. 94°-95° C. δ (360 MHz, CDCl3) 1.42 (9H, s, C(CH3)3), 2.77 (2H, br, m, ArCH2CH2NHBoc), 3.35 (2H, br, m, ArCH2CH2NHBoc), 3.61 (2H, s, ArCH2CO2H), 4.57 (1H, br, s, ArCH2CH 2 NHBoc), 7.14 (2H, d, J=7.7 Hz, ArH), 7.21 (2H, d, J=7.7 Hz, ArH); m/e (CI-) 278 (100%, m-H).

Workup

  1. customThe organic solvent was removed under vacuum
  2. additionthe residue was diluted with water (40 ml)
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. washThe combined extracts were washed with brine (1×30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-e232ebfd089d43378c8fc9c3425059b9
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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