Acetic Anhydride → HCID 178471945, compound

HRID 1396107Notes

Reaction equation

HRID 1396107 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([CH2:41][CH:42]([OH:44])[CH3:43])[CH2:40][CH2:39][CH2:38]1>C1(C)C=CC=CC=1>[OH:44][CH:42]([CH3:43])[CH2:41][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])[CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateHCID 552844011-Amino-1-(2-hydroxypropan-1-yl)cyclobutane

Product 1

HCID 178471945HCID 178471945, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (2.45 g, 9.27 mmol), Ac2O (5.30 mL, 56.1 mmol) and triethyl orthoformate (3.10 mL, 18.6 mmol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. To 1-[1-aminocyclobutyl]-2-propanol (1.20 g, 9.29 mmol) in anhydrous toluene (10 mL) was slowly added to a mixture of the residue in anhydrous toluene (30 mL) at 0° C. and stirred at room temperature for 2 hours. The solvent was removed by evaporation. Flash chromatography (AcOEt:Hexane=1:1) of the residue gave the title compound as a pale yellow solid (3.10 g, 83%). 1H-NMR (400 MHz, CDCl3) δ 0.95 (0.6H, t, J=7.3 Hz), 1.09 (2.4H, t, J=7.3 Hz), 1.29 (3H, d, J=6.1 Hz), 1.51 (1H, brs), 1.83-2.05 (4H, m), 2.18-2.35 (3H, m), 2.41-2.53 (1H, m), 3.95-4.15 (3H, m), 6.96-7.13 (1H, m), 8.27 (0.8H, d, J=14.7 Hz), 8.31 (0.2H, d, J=14.7 Hz), 10.30 (0.2H, d, J=13.4 Hz), 11.56 (0.8H, d, J=13.4 Hz).

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-f49ea1a2fff14801bd0402a5ffed3eed
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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