Triethylamine → HCID 89828092, compound

HRID 1487136Notes

Reaction equation

HRID 1487136 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.Cl.[NH:34]1[CH2:37][CH:36]([OH:38])[CH2:35]1>C1COCC1>[OH:38][CH:36]1[CH2:37][N:34]([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)[CH2:35]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 89828092HCID 89828092, compoundYield 78.2%

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 (0.5 g, 2.76 mmol), CDI (0.671 g, 4.14 mmol), the mixture was stirred for 2 hrs at 0° C. followed by addition of triethylamine (1.2154 ml, 8.28 mmol) and azetidin-3-ol hydrochloride (0.756 g, 6.90 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 (0.51 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-af44ed993b0d43c7bdfcd76f236d591c
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

Loading…