Triethylamine → 2'-deoxy-3'-O-[N-(2-n-propyl-n-pentanoyl)-glycyl]-5'-O-trityl-5-fluorouridine

HRID 728616Notes

Reaction equation

HRID 728616 reaction equation
[CH2:1]([CH:4]([CH2:12][CH2:13][CH3:14])[C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6])[CH2:2][CH3:3].C1(N=C=NC2CCCCC2)CCCCC1.[C:30]([O:49][CH2:50][C@H:51]1[O:55][C@@H:54]([N:56]2[CH:63]=[C:62]([F:64])[C:60](=[O:61])[NH:59][C:57]2=[O:58])[CH2:53][C@@H:52]1O)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:12]([CH:4]([CH2:1][CH2:2][CH3:3])[C:5]([NH:7][CH2:8][C:9]([O:11][C@@H:52]1[C@@H:51]([CH2:50][O:49][C:30]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:55][C@@H:54]([N:56]2[CH:63]=[C:62]([F:64])[C:60](=[O:61])[NH:59][C:57]2=[O:58])[CH2:53]1)=[O:10])=[O:6])[CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 1819192-(2-propylpentanoylamino)acetic AcidHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

Product 1

HCID 186469282'-deoxy-3'-O-[N-(2-n-propyl-n-pentanoyl)-glycyl]-5'-O-trityl-5-fluorouridineYield 70.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension in which 0.11 g of N-(2-n-propyl-n-pentanoyl)glycine was suspended in 15 ml of methylene chloride was added 0.11 g of dicyclohexylcarbodiimide under ice-cooling and stirring, and then the mixture was stirred under ice-cooling for one hour. Then, 0.27 g of 2'-deoxy-5'-O-trityl-5-fluorouridine, 70 mg of triethylamine and 34 mg of 4-(N,N-dimethylamino)pyridine were added to the mixture, and the mixture was reacted at room temperature for two days under stirring. Thereafter, the reaction mixture was treated according to the same method as in Reference example 5 to give 0.26 g (Yield: 70%) of the title compound.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for one hour
  4. customthe mixture was reacted at room temperature for two days
  5. stirringunder stirring
  6. additionThereafter, the reaction mixture was treated

Sources & evidence

ORD record
ord-3aee5d3ab1a34bf89812ed66c532e522
Source dataset
uspto-grants-1991_09
Patent number
US05049551

Reaction notes

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