HCID 18767798, compound → HCID 12114485, compound

HRID 2300224Notes

Reaction equation

HRID 2300224 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]1[C:40]2[NH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[C:31]([O:41][CH:42]2[O:44][C@H:43]2[CH3:45])=[CH:30][CH:29]=1>CO>[CH2:1]([N:8]([CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:10]1)[CH2:45][CH:43]([OH:44])[CH2:42][O:41][C:31]1[C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[NH:39][C:40]=2[CH:28]=[CH:29][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 18767798HCID 18767798, compoundHCID 86584414HCID 86584414, compound

Product 1

HCID 12114485HCID 12114485, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl-[1-(4-butoxy-benzenesulfonyl)-pyrrolidin-3-yl]-amine (0.16 g, 0.4 mmol) in methanol (2 ml) was added (2S)-3-(9H-carbazol-4-yloxy)-methyl oxirane (0.12 g, 0.5 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 0.28 g of an off-white solid; m.p. 73-76° C.; MS (ES) m/z 628.2 (MH+); HRMS (El) Calcd. for C36H41N3O5S (M+): 627.2767, Found: 627.2808.

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-8a5696211b444c21a138dde62d7de5b9
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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