HCID 18767786, compound → HCID 12044734, compound

HRID 2300212Notes

Reaction equation

HRID 2300212 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:12][N:11]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]1[C:39]2[NH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]=2[C:30]([O:40][CH:41]2[O:43][C@H:42]2[CH3:44])=[CH:29][CH:28]=1>CO>[CH2:1]([N:8]([CH:9]1[CH2:12][N:11]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH2:10]1)[CH2:44][CH:42]([OH:43])[CH2:41][O:40][C:30]1[C:31]2[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[NH:38][C:39]=2[CH:27]=[CH:28][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 18767786HCID 18767786, compoundHCID 86584414HCID 86584414, compound

Product 1

HCID 12044734HCID 12044734, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl-[1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl]-amine (0.14 g, 0.37 mmol) in methanol (2 ml) was added (2S)-3-(9H-carbazol-4-yloxy)-methyl oxirane (0.11 g, 0.45 mmol) and the mixture was stirred at reflux for 3 days. The methanol was then evaporated, and the residue was washed with a mixture of ether and hexanes to give 0.24 g of an off-white solid; m.p. 65-67° C.; MS (ES) m/z 614.2 (MH+); HRMS (ES) Calcd. for C35H40N3O5S (MH+): 614.2689, Found: 614.2706.

Workup

  1. temperatureat reflux for 3 days
  2. customThe methanol was then evaporated
  3. washthe residue was washed with a mixture of ether and hexanes

Sources & evidence

ORD record
ord-300d5c6808134c6c857ed8164b4530f6
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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