Acetic Anhydride → HCID 178471957, compound

HRID 1396096Notes

Reaction equation

HRID 1396096 reaction equation
[O:1]=[C:2]([C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[C:9]([F:15])[C:8]=1[F:16])[CH2:3][C:4]([O-])=O.CC(OC(C)=O)=O.[CH:24]([O:31]CC)([O:28][CH2:29][CH3:30])OCC.[NH2:34][C:35]1([CH2:39][CH2:40][OH:41])[CH2:38][CH2:37][CH2:36]1>C1(C)C=CC=CC=1>[OH:41][CH2:40][CH2:39][C:35]1([NH:34][CH:4]=[C:3]([C:2](=[O:1])[C:7]2[CH:12]=[C:11]([F:13])[C:10]([F:14])=[C:9]([F:15])[C:8]=2[F:16])[C:24]([O:28][CH2:29][CH3:30])=[O:31])[CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 552843991-AminocyclobutaneethanolHCID 77068289HCID 77068289, compound

Product 1

HCID 178471957HCID 178471957, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (3.67 g, 13.9 mmol), Ac2O (7.89 mL, 83.5 mmol) and triethyl orthoformate (4.63 mL, 27.8 mmol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. 1-amino-1-(2-hydroxyethyl)cyclobutane (1.60 g, 13.9 mmol) in anhydrous toluene (20 mL) was added slowly at 0° C. to a solution of the mixture in anhydrous toluene (50 mL). The resulting mixture was stirred at room temperature for 2 hours, and the solvent was removed by evaporation. Flash chromatography (AcOEt:Hexane=1:1) of the residue gave the title compound as a pale yellow solid (3.30 g, 61%). 1H-NMR (400 MHz, CDCl3) δ 0.96 (0.6H, t, J=7.3 Hz), 1.09 (2.4H, t, J=7.3 Hz), 1.85-2.03 (12H, m), 2.06-2.13 (2H, m), 2.20-2.30 (2H, m), 2.32-2.43 (2H, m), 3.82-3.88 (2H, m), 4.02 (0.4H, q, J=7.3 Hz), 4.07 (1.6H, q, J=7.3 Hz), 6.94-7.03 (0.2H, m), 7.05-7.13 (0.8H, m), 8.23-8.30 (1H, m), 10.05-10.17 (0.2H, m), 11.36-11.50 (0.8H, m).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customdried under high vacuum
  3. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-9ec417f605674eaaa0c78be4cb8de207
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

Loading…