Trifluoroacetic acid → HCID 86601170, compound

HRID 1173323Notes

Reaction equation

HRID 1173323 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:22])[C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O[CH2:24][NH:25][C:26](=[O:29])[CH2:27][Cl:28].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:28][CH2:27][C:26]([NH:25][CH2:24][C:6]1[C:7]([OH:22])=[C:8]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]=1[C:1]([CH3:2])([CH3:3])[CH3:4])=[O:29]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62466N-Methylol-alpha-chloroacetamideHCID 68716253HCID 68716253, compound

Product 1

HCID 86601170HCID 86601170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.0 g (9.5 mmol) of the product of Step B and 1.25 g (10.1 mmol) of N-hydroxymethyl-2-chloroacetamide in 20 mL CH2Cl2 was added 25 mL of trifluoroacetic acid. The reaction mixture was stirred under a nitrogen atmosphere overnight and then concentrated in vacuo. The residue was partitioned between EtOAc and excess saturated aqueous NaHCO3. The aqueous layer was separated and re-extracted with EtOAc. The organic layers were then combined, dried (Na2SO4), filtered and evaporated in vacuo to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and excess saturated aqueous NaHCO3
  3. customThe aqueous layer was separated
  4. extractionre-extracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-72dabaeb71494f5796ec9e5825ffc893
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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