Cytarabine → N4-[N-(cholest-5-en-3beta-oxycarbonyl)glycyl]-1-beta-D-arabinofuranosylcytosine

HRID 622728Notes

Reaction equation

HRID 622728 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][C:29]([NH:31][CH2:32][C:33](O)=[O:34])=[O:30])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C(N(CC)CC)C.C(Cl)(=O)OCC.[C@@H:49]1([N:58]2[CH:65]=[CH:64][C:62]([NH2:63])=[N:61][C:59]2=[O:60])[O:55][C@H:54]([CH2:56][OH:57])[C@@H:52]([OH:53])[C@@H:50]1[OH:51]>O1CCCC1.CN(C)C=O>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][C:29]([NH:31][CH2:32][C:33]([NH:63][C:62]4[CH:64]=[CH:65][N:58]([C@@H:49]5[O:55][C@H:54]([CH2:56][OH:57])[C@@H:52]([OH:53])[C@@H:50]5[OH:51])[C:59](=[O:60])[N:61]=4)=[O:34])=[O:30])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

7

Reactant 4

HCID 6253CytarabineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14168269N-(cholest-5-en-3beta-oxycarbonyl)glycine

Product 1

HCID 14208547N4-[N-(cholest-5-en-3beta-oxycarbonyl)glycyl]-1-beta-D-arabinofuranosylcytosineYield 44.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of N-(cholest-5-en-3β-oxycarbonyl)glycine (2.74 g) and triethylamine (0.78 ml) in tetrahydrofuran (40 ml) was added dropwise ethyl chlorocarbonate (0.61 g) at -15° C., and the reaction mixture was stirred for 20 minutes at -15° C. To the reaction mixture a solution of 1-β-D-arabinofuranosylcytosine (1.37 g) in dimethylformamide (30 ml) was added dropwise at -15° C. to -10° C. After the addition, the mixture was stirred for one hour at 5° C. and then for 30 minutes at room temperature. The reaction mixture was concentrated in vacuo. The residue was washed with methanol and dried to afford a crude reaction product, which was purified by silica gel column chromatography to yield N4 -[N-(cholest-5-en-3β-oxycarbonyl)glycyl]-1-β-D- arabinofuranosylcytosine (1.8 g) as a white powder.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred for one hour at 5° C.
  3. waitfor 30 minutes at room temperature
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. washThe residue was washed with methanol
  6. customdried
  7. customto afford a crude
  8. customreaction product, which
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e25b054649a944d293bede677fed3af5
Source dataset
uspto-grants-1988_09
Patent number
US04772594

Reaction notes

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