Triethylamine → HCID 89828081, compound

HRID 1487132Notes

Reaction equation

HRID 1487132 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1N=CN([C:19]([N:21]2C=N[CH:23]=[CH:22]2)=O)C=1.C(N(CC)CC)C.Cl.N1CCC1>C1COCC1>[N:21]1([C:11](=[O:13])[CH2:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:19][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 12308726Azetidine hydrochloride

Product 1

HCID 89828081HCID 89828081, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

THF (30 mL) was added to a mixture of 2-(3-Nitrophenyl)acetic acid (1 g, 5.52 mmol) and CDI (1.34 g, 8.28 mmol), the mixture was stirred for 2 hrs at 0° C. followed by addition of triethylamine (2.308 ml, 16.56 mmol) and azetidine hydrochloride (1.033 g, 11.04 mmol). The reaction mixture was stirred for 12 hrs at room temperature and then concentrated under vacuum. The crude residue was purified by column chromatography using 0-50% ethyl acetate in hexanes as eluent to afford the title product (0.53 g).

Workup

  1. stirringThe reaction mixture was stirred for 12 hrs at room temperature
  2. concentrationconcentrated under vacuum
  3. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-c4fb91bf90214047ac40d8861017b160
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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