Potassium Carbonate → 2-[2-(2-Benzyloxycarbonylmethoxy-5-chloro-benzyl)-4-chloro-phenoxy]-propionic acid tert-butyl ester

HRID 2244471Notes

Reaction equation

HRID 2244471 reaction equation
[C:1]([O:5][C:6](=[O:10])[CH:7](Br)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:11]([O:18][C:19](=[O:38])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[CH2:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[OH:37])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:10])[CH:7]([O:37][C:31]1[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:30]=1[CH2:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[O:21][CH2:20][C:19]([O:18][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:38])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 545327tert-Butyl 2-bromopropanoateHCID 68450956[4-Chloro-2-(5-chloro-2-hydroxy-benzyl)-phenoxy]-acetic acid benzyl ester

Product 1

HCID 684523432-[2-(2-Benzyloxycarbonylmethoxy-5-chloro-benzyl)-4-chloro-phenoxy]-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromopropionic acid tert-butyl ester (0.827 g, 3.95 mmol) in DMF (15 mL) is added [4-chloro-2-(5-chloro-2-hydroxy-benzyl)-phenoxy]-acetic acid benzyl ester (1.5 g, 3.60 mmol) and potassium carbonate (0.547 g, 3.95 mmol). The reaction mixture is stirred at RT overnight and the solvent is removed in vacuo. The crude product is dissolved in EtOAc (50 mL) and washed with water (50 mL) and brine (50 mL). The organic portion is dried (MgSO4) and concentrated in vacuo to yield a yellow oil which is dried in a vacuum oven for 2 hours to afford the titled product which is used in the next step without purification.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe crude product is dissolved in EtOAc (50 mL)
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialThe organic portion is dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a yellow oil which
  7. customis dried in a vacuum oven for 2 hours

Sources & evidence

ORD record
ord-334a1de74ba8476988e3f704cf112cee
Source dataset
uspto-grants-2010_03
Patent number
US07678826B2

Reaction notes

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