Acetic Anhydride → HCID 136167174, compound

HRID 646522Notes

Reaction equation

HRID 646522 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([CH2:29][NH2:30])[C:25]=1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)C1C=CC=CC=1.[C:38](OC(=O)C)(=[O:40])[CH3:39].C(N(CC)CC)C.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:23][C:12]1[C:13]([OH:15])=[CH:14][C:9]([OH:8])=[C:10]([C:24]2[O:28][N:27]=[C:26]([CH2:29][NH:30][C:38](=[O:40])[CH3:39])[C:25]=2[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 25135Boron TrichlorideHCID 59264757HCID 59264757, compound

Product 1

HCID 136167174HCID 136167174, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of C-[5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-(4-fluoro-phenyl)-isoxazol-3-yl]-methylamine (100 mg, 0.19 mmol) in DCM was added acetic anhydride (130 μl, 7.0 equiv.) and triethylamine (81 μl, 3.0 equiv.). The solution was stirred at room temperature until the amine was consumed. The solvent was removed in vacuo to leave the yellow tinged oily crude benzyl protected product. This was deprotected using the standard procedure with boron trichloride described above and purified by preparative TLC and soxhlet extraction of the silica by ether gave the pure compound as a colourless solid (10 mg, 14% yield).

Workup

  1. customwas consumed
  2. customThe solvent was removed in vacuo
  3. customto leave the yellow tinged oily crude benzyl protected product
  4. custompurified by preparative TLC
  5. extractionextraction of the silica by ether

Sources & evidence

ORD record
ord-af924a9c00664060b7999fd3e49693bb
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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