Trifluoroacetic acid → HCID 25016282, compound

HRID 600848Notes

Reaction equation

HRID 600848 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:18][C@H:19]2[CH2:23][O:22][C:21]([NH2:24])=[N:20]2)CC2C=CC(OC)=CC=2)[CH:5]=[CH:6][CH:7]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:18][C@H:19]2[CH2:23][O:22][C:21]([NH2:24])=[N:20]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57667109HCID 57667109, compound

Product 1

HCID 25016282HCID 25016282, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-4-{[(3-chloro-phenyl)-(4-methoxy-benzyl)-amino]-methyl}-4,5-dihydro-oxazol-2-ylamine (97 mg) at r.t. in dichloromethane (10 ml) were added anisole (0.31 ml) and trifluoroacetic acid (2.74 ml). The mixture was stirred at r.t. for 48 h and was then concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated aq. sodium bicarbonate solution, the phases were separated, and the organic phase was dried and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient:dichloromethane->dichloromethane/methanol 85:15) to give (S)-4-[(3-chloro-phenylamino)-methyl]-4,5-dihydro-oxazol-2-ylamine (22 mg, 35%) as a white gum. MS (ISP): 228.1 ([{37Cl}M+H]+), 226.2 ([{35Cl}M+H]+)

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and saturated aq. sodium bicarbonate solution
  3. customthe phases were separated
  4. customthe organic phase was dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2; gradient:dichloromethane->dichloromethane/methanol 85:15)

Sources & evidence

ORD record
ord-56b88c1806784dc0809c0dddd56b586b
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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