Hydrochloric Acid → HCID 67086928, compound

HRID 1665172Notes

Reaction equation

HRID 1665172 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:8][CH:7]=1.[OH-].[Li+].Cl.CCOC(C)=O>C1COCC1.C(Cl)Cl>[C:17]([O:16][C:14]([CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([OH:21])=[O:2])=[CH:11][CH:10]=1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl Acetate2×HCID 67086798HCID 67086798, compound

Product 1

HCID 67086928HCID 67086928, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-tert-Butoxycarbonylmethoxy-phenyl)-propionic acid methyl ester (2.70 g, 9.17 mmol) in THF (80 ml) is added 0.2N lithium hydroxide (45.9 ml, 9.17 mmol) at 0° C. and the reaction mixture is stirred at 0° C. for 4.5 hours. 1M HCl (15 ml) is added and the product is extracted using EtOAc (×3). The organic phase is dried (Na2SO4) and concentrated in vacuo to yield a white solid. Flash chromatography (SiO2, 10% EtOAc in CH2Cl2, then 20% EtOAc in CH2Cl2) yields 3-(4-tert-Butoxycarbonylmethoxy-phenyl)-propionic acid as a white solid.

Workup

  1. extractionthe product is extracted
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto yield a white solid

Sources & evidence

ORD record
ord-002c71273f704466b230f83001dd1d63
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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