Methanol → Methyl 1-[(4-iodophenyl)sulfonyl]azetidine-3-carboxylate

HRID 1913168Notes

Reaction equation

HRID 1913168 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:18](N(CC)CC)C.S(Cl)(Cl)=O.CO>C1COCC1.CCOC(C)=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 584945631-[(4-Iodophenyl)sulfonyl]azetidine-3-carboxylic acid

Product 1

HCID 58494513Methyl 1-[(4-iodophenyl)sulfonyl]azetidine-3-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-[(4-iodophenyl)sulfonyl]azetidine-3-carboxylic acid (0.75 g, 2.06 mmol) in THF (15 mL) is added triethylamine (0.43 mL, 3.09 mmol) followed by thionyl chloride (0.18 mL, 2.47 mmol). After stirring for 1 h, MeOH (10 mL) is added. Stirring is continued for another 1 h. The reaction mixture is concentrated under reduced pressure to give a residue which is taken up in EtOAc and washed with saturated aqueous NaHCO3. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure to give 0.60 g (77%) of methyl 1-[(4-iodophenyl)sulfonyl]azetidine-3-carboxylate. m/z=382 [M++H].

Workup

  1. stirringStirring
  2. waitis continued for another 1 h
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customto give a residue which
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialThe organic layer is dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f53bb7310bf4137aa9a349e0eae0e24
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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