Chlorambucil → HCID 131722767, compound

HRID 1384748Notes

Reaction equation

HRID 1384748 reaction equation
CC(C)N=C=NC(C)C.[CH:10]1[C:15]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[C:12]([N:22]([CH2:26][CH2:27][Cl:28])[CH2:23][CH2:24][Cl:25])[CH:11]=1.[CH3:29][CH:30]([CH2:32][CH2:33][CH2:34][C@H:35]([C@@H:37]1[C@:55]2([CH3:56])[C@H:40]([C@H:41]3[C@H:52]([CH2:53][CH2:54]2)[C@:50]2([CH3:51])[C:44]([CH2:45][C@H:46]([CH2:48][CH2:49]2)[OH:47])=[CH:43][CH2:42]3)[CH2:39][CH2:38]1)[CH3:36])[CH3:31].C(=O)(O)[O-].[Na+]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:31][CH:30]([CH2:32][CH2:33][CH2:34][C@H:35]([C@@H:37]1[C@:55]2([CH3:56])[C@H:40]([C@H:41]3[C@H:52]([CH2:53][CH2:54]2)[C@:50]2([CH3:51])[C:44]([CH2:45][C@H:46]([CH2:48][CH2:49]2)[OH:47])=[CH:43][CH2:42]3)[CH2:39][CH2:38]1)[CH3:36])[CH3:29].[Cl:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][Cl:28])[C:12]1[CH:11]=[CH:10][C:15]([CH2:16][CH2:17][CH2:18][C:19]([O-:21])=[O:20])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 2708ChlorambucilHCID 5997CholesterolHCID 12734DiisopropylcarbodiimideHCID 516892Sodium Bicarbonate

Product 1

HCID 131722767HCID 131722767, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

DIC (170 μl, 1.10 mmol) was added to a solution of chlorambucil (669 mg, 2.20 mmol) in dry dichloromethane (15 ml). The mixture was stirred at room temperature for 0.5 hour and added to a solution of cholesterol (387 mg, 1.00 mmol) and DMAP (122 mg, 1.00 mmol) in dichloromethane (10 ml). The reaction mixture was stirred overnight and then poured onto 5% sodium bicarbonate. The phases were separated and the organic phase was washed with brine and dried (MgSO4). The solution was filtered and concentrated and the product was purified by column chromatography (silica, chloroform) to give 560 mg (83%)of colouless oil. The product was characterised by MALDI mass spectrometry, giving M+H at 674 as expected. Further characterisation was carried out using 1H (500 MHz) and 13C (125 MHz) NMR analysis, giving spectra in accordance with the structure.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customthe product was purified by column chromatography (silica, chloroform)

Sources & evidence

ORD record
ord-650ece3898324ba9a0a8574e9c803182
Source dataset
uspto-grants-2001_07
Patent number
US06261537B1

Reaction notes

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