Triethylamine → 3-(2-Iodo-phenylcarbamoyl)-azetidine-1-carboxylic acid benzyl ester
Reaction equation
[I:1]NC1C=CC=CC=1.F[P-](F)(F)(F)(F)F.[N:16]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2N=N1.[CH2:36]([O:43][C:44]([N:46]1[CH2:49][CH:48]([C:50]([OH:52])=O)[CH2:47]1)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[CH2:36]([O:43][C:44]([N:46]1[CH2:49][CH:48]([C:50](=[O:52])[NH:16][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[I:1])[CH2:47]1)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To 1.0 g (4.57 mmol) iodoaniline in 30 mL acetonitrile were added 2.22 g (5.02 mmol) BOP, 1.78 g (4.57 mmol) azetidine-1,3-dicarboxylic acid monobenzyl ester (route 13, step a), 0.6 mL (4.57 mmol) triethylamine, and the mixture was stirred at room temperature for 16 hours. 0.6 mL (4.57 mmol) triethylamine was added and the mixture was stirred for 2 hours. 2.22 g (5.02 mmol) BOP was added and the mixture was stirred at room temperature for 16 hours. 30 mL 1 M aqueous Na2CO3 was added and the mixture was extracted with EtOAc (2×30 mL), the organic layers were combined, washed with 30 mL brine then dried with Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 7:3).
Workup
- stirringthe mixture was stirred for 2 hours
- stirringthe mixture was stirred at room temperature for 16 hours
- extractionthe mixture was extracted with EtOAc (2×30 mL)
- washwashed with 30 mL brine
- dry with materialthen dried with Na2SO4
- filtrationAfter filtration and evaporation of the solvent the product
- customwas purified by column chromatography (silica, heptane/EtOAc 7:3)
Sources & evidence
- ORD record
- ord-4d605f15ccd44d6ab539dec074437487
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346816B2
Reaction notes
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