Diisopropylethylamine → tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16]N(C)CCCN=C=NCC.O.[OH:28][N:29]1[C:33]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:16][O:28][N:29]([CH3:33])[C:12]([CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:11]1)=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (D25) (5 g, 24.85 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (14.39 g, 75.55 mmol), 1-hydroxybenzotriazole hydrate (0.38 g, 2.48 mmol) and N,N-diisopropylethylamine (34.6 ml, 198 mmol) in dimethylformamide (80 ml) was stirred overnight at room temperature. The reaction mixture was then concentrated to half volume in vacuo, poured into water (60 ml) and extracted with ethylacetate (3×60 ml). The combined organic phases were washed with saturated aqueous NH4Cl (100 ml), saturated aqueous NaHCO3 (100 ml), water and brine (100 ml), dried with Na2SO4 anhydrous (50 g) and concentrated under reduced atmosphere. Collected organics after solvent evaporation afforded the title compound (D26) (5.33 g)
Workup
- concentrationThe reaction mixture was then concentrated to half volume in vacuo
- additionpoured into water (60 ml)
- extractionextracted with ethylacetate (3×60 ml)
- washThe combined organic phases were washed with saturated aqueous NH4Cl (100 ml), saturated aqueous NaHCO3 (100 ml), water and brine (100 ml)
- dry with materialdried with Na2SO4 anhydrous (50 g)
- concentrationconcentrated under reduced atmosphere
- customCollected organics after solvent evaporation
Sources & evidence
- ORD record
- ord-42b3c6e45f714d7a89c6106a2a386ac7
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08828987B2
Reaction notes
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