(S)-(+)-4-(2,3-Epoxypropoxy)carbazole → (S)-4-[2-Hydroxy-3-([4-(phenylsulfonamido)phenyl]-2-methylpropylamino)propoxy]carbazole

HRID 1824327Notes

Reaction equation

HRID 1824327 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.CC(N)(C)C[C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:24][CH:23]=1>C(O)C>[OH:1][C@@H:2]([CH2:3][N:11]([C:22]1[CH:23]=[CH:24][C:25]([NH:28][S:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)(=[O:30])=[O:31])=[CH:26][CH:27]=1)[CH2:10][CH:18]([CH3:6])[CH3:17])[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazoleHCID 22147701N-(4-[2-Methyl-2-aminopropyl]phenyl)benzenesulfonamide

Product 1

HCID 53953669(S)-4-[2-Hydroxy-3-([4-(phenylsulfonamido)phenyl]-2-methylpropylamino)propoxy]carbazoleYield 134.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-4-(oxiranylmethoxy)-9H-carbazole (1.0 g, 4.18 mmol) and N-(4-[2-methyl-2-aminopropyl]phenyl)benzenesulfonamide (1.9 g, 6.24 mmol) in absolute ethanol (100 mL) was refluxed for 18 h. The solvent was removed under vacuum and the residue was purified by column chromatography eluting with chloroform:methanol (95:5). Concentration of the appropriate fractions provided 1.53 g (69%) of the desired product. MS (FD) m/e 544.3 (MH+); Anal. Calcd. for C31H33N3O4S: C, 68.48; H, 6.12; N, 7.73. Found: C, 68.49; H, 6.02; N, 7.53.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by column chromatography
  3. washeluting with chloroform:methanol (95:5)

Sources & evidence

ORD record
ord-a80781d959a64abc97dad2ce1eb0971f
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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