Triethylamine → HCID 89815274, compound

HRID 1487134Notes

Reaction equation

HRID 1487134 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(N2C=NC=C2)=O)C=1.C(N(CC)CC)C.[O:33]1[CH2:36][CH:35]([NH2:37])[CH2:34]1>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:37][CH:35]2[CH2:36][O:33][CH2:34]2)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 98339233-Oxetanamine

Product 1

HCID 89815274HCID 89815274, compoundYield 47.9%

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 (0.8 g, 4.42 mmol), CDI (1.07 g, 8.28 mmol), the mixture was stirred for 2 hrs at 0° C. followed by addition of triethylamine (1.8 ml, 13.25 mmol) and oxetan-3-amine (0.484 g, 6.62 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 (0.5 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-080f8f7759fc4a079add1a1c24c3f215
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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