Trifluoroacetic acid → HCID 59131010, compound

HRID 1992681Notes

Reaction equation

HRID 1992681 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]\[C:11]([OH:13])=[O:12].FC(F)(F)C(O)=O.CO[CH2:23][N:24]([CH2:29][Si](C)(C)C)[C:25]([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([N:24]1[CH2:29][C@@H:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[C@@H:10]([C:11]([OH:13])=[O:12])[CH2:23]1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 22228418N-tert-Butyl-N-(methoxymethyl)-N-(trimethylsilylmethyl)amineHCID 59130999HCID 59130999, compound

Product 1

HCID 59131010HCID 59131010, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2Z)-3-(2,4-difluorophenyl)acrylic acid, from preparation 35 (400 mg, 2.17 mmol) and trifluoroacetic acid (17 μL, 0.2 mmol) in dichloromethane (1 mL) was added N-(methoxymethyl)-2-methyl-N-[(trimethylsilyl)methyl]propan-2-amine, from preparation 23 (882 mg, 4.35 mmol) over 30 minutes at 0° C. The reaction mixture was warmed to room temperature and stirred for 24 hours. The solvent was removed in vacuo and the white residue formed was triturated with diethyl ether (5 mL) and the solid filtered off to give the desired product, 400 mg (65%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe white residue formed
  3. customwas triturated with diethyl ether (5 mL)
  4. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-2c8b65f87ae54e1c8a698082622241ec
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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