Hydrochloric Acid → HCID 67422368, compound

HRID 2070054Notes

Reaction equation

HRID 2070054 reaction equation
C([Li])CCC.[C:6]([N:13]1[CH2:16][C:15](=[O:17])[CH2:14]1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl.[CH2:19]([O:26][C:27]1[CH:32]=[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:30]=[CH:29][C:28]=1Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.CCCCCC>[C:9]([O:8][C:6]([N:13]1[CH2:16][C:15]([C:30]2[CH:29]=[CH:28][C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:32][C:31]=2[O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([OH:17])[CH2:14]1)=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 128821681,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzeneHCID 178418339Butyllithium

Product 1

HCID 67422368HCID 67422368, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

In a 100 ml three-necked flask, 5 g of 2,4-bis(benzyloxy)-1-bromobenzene are dissolved in 60 ml of tetrahydrofuran. The mixture is cooled to −70° C. and then 11.4 ml of 2.5M n-butyllithium in hexane are added. The reaction medium is stirred at −70° C. for 1 hour, and then 2.8 g of 1-Boc-azetidine-3-one dissolved in 4 ml of THF are added dropwise. The reaction medium is stirred at −70° C. for 2 hours and then left at ambient temperature overnight. The reaction medium is poured into 40 ml of a 2M solution of hydrochloric acid and then extracted with 100 ml of ethyl acetate. The organic phases are combined, washed with 50 ml of water and then dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel (AnaLogix SF40-80 g column), elution being carried out with 80/20 heptane/ethyl acetate. 2.2 g of 3-(2,4-bis(benzyloxy)phenyl)-3-hydroxyazetidine-1-carboxylic acid tert-butyl ester are obtained. Yield: 37%.

Workup

  1. additionare added dropwise
  2. stirringThe reaction medium is stirred at −70° C. for 2 hours
  3. waitleft at ambient temperature overnight
  4. extractionextracted with 100 ml of ethyl acetate
  5. washwashed with 50 ml of water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue is chromatographed on silica gel (AnaLogix SF40-80 g column), elution

Sources & evidence

ORD record
ord-bc0d3c987a734bbbb3fa2cb8404b92df
Source dataset
uspto-grants-2012_10
Patent number
US08299259B2

Reaction notes

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