m-Chloroperbenzoic acid → 3-(4-Hydroxy-2'-methyl-biphenyl-3-yloxy)-azetidine-1-carboxylic acid tert-butyl ester

HRID 2038456Notes

Reaction equation

HRID 2038456 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[CH:16]=[CH:17][C:18]=2C=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[CH:16]=[CH:17][C:18]=2[OH:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866570473-(4-Formyl-2'-methyl-biphenyl-3-yloxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673443903-(4-Hydroxy-2'-methyl-biphenyl-3-yloxy)-azetidine-1-carboxylic acid tert-butyl esterYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (6 mL) solution of the title compound of Step A (1.40 g, 3.81 mmol) was added m-CPBA (77 wt %, 1.30 g, 5.70 mmol). After 15 h, 10 wt % Na2S2O5 (aq.) was added and the solution allowed to stir until the aqueous was KI paper negative and extracted with CH2Cl2 (2×). The combined organic layers were washed with saturated NaHCO3 (aq.), concentrated and treated with MeOH (30 mL) and 1N NaOH (15 mL). After 15 h, the reaction was partially concentrated to remove the MeOH and acidified with 1M KHSO4 then extracted with EtOAc (2×). The combined organic layers were dried and concentrated to give the 1.1 g of the title compound that was used in the next step without further purification.

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. washThe combined organic layers were washed with saturated NaHCO3 (aq.)
  3. concentrationconcentrated
  4. additiontreated with MeOH (30 mL) and 1N NaOH (15 mL)
  5. waitAfter 15 h
  6. concentrationthe reaction was partially concentrated
  7. customto remove the MeOH
  8. extractionthen extracted with EtOAc (2×)
  9. customThe combined organic layers were dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0a4ab31067e441f6999e9f05392033b7
Source dataset
uspto-grants-2013_11
Patent number
US08575364B2

Reaction notes

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