Benzyl chloroformate → N-carbobenzyloxy-3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)-3-hydroxyazetidine

HRID 1637855Notes

Reaction equation

HRID 1637855 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:12]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2([OH:46])[CH2:32][N:31](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:30]2)=[C:25]([F:47])[CH:24]=1)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>C1C=CC=CC=1>[C:2]([N:31]1[CH2:32][C:29]([C:26]2[CH:27]=[CH:28][C:23]([NH:22][C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[CH:24][C:25]=2[F:47])([OH:46])[CH2:30]1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 226256753-(N-Carbobenzyloxy-3-fluoroanilin-4-yl)-3-hydroxy-1-(1,1-diphenylmethyl)azetidine

Product 1

HCID 22625688N-carbobenzyloxy-3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)-3-hydroxyazetidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzyl chloroformate (3.8 mL, 26.6 mmol) was added to a solution of 3-(N-carbobenzyloxy-3-fluoroanilin-4-yl)-3-hydroxy-1-(1,1-diphenylmethyl)azetidine (Example 81, Step 2, 1.60 g, 3.32 mmol) in benzene (30 mL) and then heated under reflux under nitrogen for 2 hr. The benzene was evaporated and the residue chromatographed over silica gel (150 g, 40-60 μm) eluting with 20-60% ethyl acetate-hexane. The title compound was obtained as a white foam. 1H NMR δ (CDCl3): 3.32, 4.19, 4.42, 5.08, 5.17, 6.98, 7.11, 7.19, 7.24-7.43.

Workup

  1. temperatureheated
  2. temperatureunder reflux under nitrogen for 2 hr
  3. customThe benzene was evaporated
  4. customthe residue chromatographed over silica gel (150 g, 40-60 μm)
  5. washeluting with 20-60% ethyl acetate-hexane

Sources & evidence

ORD record
ord-92e3209a49ca407b9c757906527c5b91
Source dataset
uspto-grants-2000_03
Patent number
US06043266

Reaction notes

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