Acetic Anhydride → HCID 178471958, compound

HRID 1396097Notes

Reaction equation

HRID 1396097 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[C:10]=1[F:18])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:19]C(OC(C)=O)=O.C(OCC)(OCC)OCC.[NH2:36][C:37]1([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][CH2:39][CH2:38]1>C1(C)C=CC=CC=1>[OH:44][CH2:43][CH2:42][C:37]1([NH:36][CH:19]=[C:3]([C:2](=[O:1])[C:9]2[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([F:17])[C:10]=2[F:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateHCID 552909312-(1-Aminocyclopentyl)ethan-1-ol

Product 1

HCID 178471958HCID 178471958, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (20.3 g, 76.8 mmol), Ac2O (44.0 mL, 0.465 mol) and triethyl orthoformate (25.6 mL, 0.154 mol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. 1-amino-1-(2-hydroxyethyl)cyclopentane (9.94 g, 76.9 mmol) in anhydrous toluene (50 mL) was slowly added to a solution of the mixture in anhydrous toluene (200 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 hours. The solvent was removed by evaporation. Flash chromatography (AcOEt:Hexane=2:1) of the residue gave the title compound as a colorless solid (23.2 g, 75%). 1H-NMR (400 MHz, CDCl3) δ 0.96 (0.6H, t, J=7.3 Hz), 1.09 (2.4H, t, J=7.3 Hz), 1.48-1.54 (1H, m), 1.74-1.90 (6H, m), 1.97-2.06 (4H, m), 3.78-3.85 (2H, m), 3.98-4.10 (2H, m), 6.95-7.12 (1H, m), 8.17-8.24 (1H, m), 9.81-9.94 (0.3H, m), 11.20-11.35 (0.7H, 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-520cf127af2f4c83b6af66db9779a6a4
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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