Thymidine → HCID 15613767, compound

HRID 382229Notes

Reaction equation

HRID 382229 reaction equation
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.ClCCl.[C:21](Cl)([O:23][CH2:24][CH:25]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22]>N1C=CC=CC=1>[C:21]([O:7][CH2:6][C@H:5]1[O:8][C@@H:1]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2][C@@H:3]1[OH:4])([O:23][CH2:24][CH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]2[C:37]1=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:22]

Participants

5

Reactant 3

HCID 5789Thymidine2×HCID 6344DichloromethaneHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 15613767HCID 15613767, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Thymidine (10 mmol) was dried by coevaporation with dry pyridine (2×30 ml), re-dissolved in dry pyridine (50 ml) and cooled using an acetone/carbon dioxide bath to a temperature of −20° C. The thymidine solution was magnetically stirred and a dichloromethane solution of FMOC-Cl (12 mmol, 1.2 eq. in 20 ml DCM) was added over a period of 60 minutes. The reaction mixture was warmed to room temperature and stirred for additional 60 minutes. The reaction mixture was partitioned between saturated sodium hydrogen carbonate (250 ml) and dichloromethane (3×100 ml). The organic phase was saved, combined, evaporated and dried by coevaporation with toluene (2×50 ml) forming an oily residue. A pure product was crystallized from the oily residue using dichloromethane (30 ml) and benzene (50 ml) as solvent. Yield 76%—white crystals.

Workup

  1. temperaturecooled
  2. customto a temperature of −20° C
  3. customThe reaction mixture was partitioned between saturated sodium hydrogen carbonate (250 ml) and dichloromethane (3×100 ml)
  4. customevaporated
  5. dry with materialdried by coevaporation with toluene (2×50 ml)
  6. customforming an oily residue
  7. customA pure product was crystallized from the oily residue

Sources & evidence

ORD record
ord-bad1a40fcfb54829b8b04b960aa73179
Source dataset
uspto-grants-2001_10
Patent number
US06309836B1

Reaction notes

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