Benzylamine → HCID 9827680, compound

HRID 1787533Notes

Reaction equation

HRID 1787533 reaction equation
[OH:1][C@@:2]([CH3:31])([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[C:27]3[S:28][CH:29]=[CH:30][C:26]=3[O:25][N:24]=2)[CH:18]=1)[CH2:3]OS(C1C=CC(C)=CC=1)(=O)=O.[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[CH2:32]([NH:39][CH2:3][C@@:2]([CH3:31])([OH:1])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[C:27]3[S:28][CH:29]=[CH:30][C:26]=3[O:25][N:24]=2)[CH:18]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 9825448HCID 9825448, compound

Product 1

HCID 9827680HCID 9827680, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Stir a solution of toluene-4-sulfonic acid (S)-2-hydroxy-2-methyl-3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propyl ester (intermediate prepared as described in example 6, 2.45 g, 0.00533 g) and tetrahydrofuran (40 mL), and treat dropwise at 0° C. with a solution of benzylamine (0.57 g, 0.00533 mol, Aldrich Chemical Company) and tetrahydrofuran (10 mL). Stir overnight at room temperature, concentrate in vacuo and partition the residue between ethyl acetate (100 mL) and water (100 mL). Separate the organic phase, dry (MgSO4), filter and concentrate in vacuo. Purify the residue by flash chromatography (silica gel, elute with 9:1 dichloromethane:methanol) to give the free base of the title compound. The maleate salt may be prepared as described for example 66.

Workup

  1. concentrationconcentrate in vacuo
  2. custompartition the residue between ethyl acetate (100 mL) and water (100 mL)
  3. customSeparate the organic phase
  4. dry with materialdry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue
  8. washby flash chromatography (silica gel, elute with 9:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-8154983b4307406c94de9f9dec4593b3
Source dataset
uspto-grants-2009_03
Patent number
US07511046B2

Reaction notes

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