Diisopropylethylamine → HCID 40013524, compound

HRID 1487103Notes

Reaction equation

HRID 1487103 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:21]([CH2:25][CH3:26])[CH:22](C)C)(C)C.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.N1CCC1>CN(C=O)C.O>[N:21]1([C:12]([C:11]2[CH:10]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:17]=[CH:16][CH:15]=2)=[O:14])[CH2:22][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 8541623-(((Tert-butoxy)carbonyl)amino)benzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12308726Azetidine hydrochloride

Product 1

HCID 40013524HCID 40013524, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-((tert-butoxycarbonyl)amino)benzoic acid (1.5 g, 6.32 mmol) in DMF (15 ml) were added N,N-diisopropyl ethylamine (2.208 ml, 12.64 mmol) and o-Benzotriazol-1-yl-tetramethyluronium hexafluorophosphate (2.398 g, 6.32 mmol) followed by azetidine hydrochloride (1.183 g, 12.64 mmol) at room temperature, under nitrogen atmosphere. The reaction was stirred at room temperature for 24 h and monitored by TLC. To the reaction mixture, water (25.0 ml) was added and extracted with ethyl acetate (30 ml×3). The aqueous layer was re-extracted with ethyl acetate. All organic layers were combined and washed with cold water (20.0 ml) and brine (20 ml); dried over sodium sulphate and solvent was evaporated under vacuum to get the titled compound (1.1 gm).

Workup

  1. extractionextracted with ethyl acetate (30 ml×3)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate
  3. washwashed with cold water (20.0 ml) and brine (20 ml)
  4. dry with materialdried over sodium sulphate and solvent
  5. customwas evaporated under vacuum

Sources & evidence

ORD record
ord-1ef01ca0ffa6474684f25d56f5d0b190
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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