Chlorambucil → HCID 131722767, compound

HRID 2270040Notes

Reaction equation

HRID 2270040 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, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

DIC (170 μl, 1.10 mmol) was added to a solution of chlorambucil (Sigma, 669 mg, 2.20 mmol) in dry dichloromethane (15 ml). The mixture was stirred at room temperature for 0.5 h and added to a solution of cholesterol (Aldrich, 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%) yield 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)
  8. customto give 560 mg (83%) yield of colouless oil
  9. customgiving M+H at 674
  10. customgiving spectra in accordance with the structure

Sources & evidence

ORD record
ord-07b002564573435f86a180cfaa41bffc
Source dataset
uspto-grants-2001_12
Patent number
US06331289B1

Reaction notes

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