Trifluoroacetic acid → N-Carbobenzyloxy-3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)azetidine

HRID 1637856Notes

Reaction equation

HRID 1637856 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[C:15]([N:25]1[CH2:28][C:27]([C:30]2[CH:46]=[CH:45][C:33]([NH:34][C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])=[CH:32][C:31]=2[F:47])(O)[CH2:26]1)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)Cl>[C:15]([N:25]1[CH2:26][CH:27]([C:30]2[CH:46]=[CH:45][C:33]([NH:34][C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])=[CH:32][C:31]=2[F:47])[CH2:28]1)([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22625688N-carbobenzyloxy-3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)-3-hydroxyazetidine

Product 1

HCID 22625683N-Carbobenzyloxy-3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)azetidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (30 mL) and trifluoroacetic acid (12 mL) were added to a solution of N-carbobenzyloxy-3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)-3-hydroxyazetidine (Example 81, Step 3, 4.3 g, 9.55 mmol) in methylene chloride (40 mL) and stirred for 2 days. Removal of the solvents at 45°/0.75 mm gave an amber oil. Chromatography over silica gel (150 g, 40-60 μm) eluting with 1-3% methanol-chloroform yielded the title compound as a solid, m.p. 95°.

Workup

  1. customRemoval of the solvents at 45°/0.75 mm
  2. customgave an amber oil
  3. washChromatography over silica gel (150 g, 40-60 μm) eluting with 1-3% methanol-chloroform

Sources & evidence

ORD record
ord-5fa3c3791f0f475c83d2d8727da11a61
Source dataset
uspto-grants-2000_03
Patent number
US06043266

Reaction notes

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