N,N-diethyl-beta-alanine hydrochloride → 3'-O-(5-chloro-2-thenyl)-2'-deoxy-5'-O-[3-(diethylamino)propanoyl]-5-fluorouridine 2,4,6-triisopropylbenzenesulfonate

HRID 981730Notes

Reaction equation

HRID 981730 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][O:8][C@@H:9]2[C@@H:13]([CH2:14][OH:15])[O:12][C@@H:11]([N:16]3[CH:23]=[C:22]([F:24])[C:20](=[O:21])[NH:19][C:17]3=[O:18])[CH2:10]2)=[CH:4][CH:3]=1.Cl.[CH2:26]([N:28]([CH2:34][CH3:35])[CH2:29][CH2:30][C:31](O)=[O:32])[CH3:27].[CH:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[C:41]([CH:49]([CH3:51])[CH3:50])[C:40]=1C(C)C)([CH3:38])[CH3:37]>N1C=CC=CC=1>[CH:49]([C:41]1[CH:40]=[C:39]([CH:36]([CH3:37])[CH3:38])[CH:44]=[C:43]([CH:30]([CH3:29])[CH3:31])[C:42]=1[S:45]([OH:46])(=[O:47])=[O:8])([CH3:50])[CH3:51].[Cl:1][C:2]1[S:6][C:5]([CH2:7][O:8][C@@H:9]2[C@@H:13]([CH2:14][O:15][C:31](=[O:32])[CH2:30][CH2:29][N:28]([CH2:34][CH3:35])[CH2:26][CH3:27])[O:12][C@@H:11]([N:16]3[CH:23]=[C:22]([F:24])[C:20](=[O:21])[NH:19][C:17]3=[O:18])[CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3084241N,N-diethyl-beta-alanine hydrochlorideHCID 11514985Triisopropylbenzenesulfonyl chlorideHCID 148495883'-O-(5-chloro-2-thenyl)-2'-deoxy-5-fluorouridine

Product 1

HCID 148496563'-O-(5-chloro-2-thenyl)-2'-deoxy-5'-O-[3-(diethylamino)propanoyl]-5-fluorouridine 2,4,6-triisopropylbenzenesulfonateYield 92.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.00 g of 3'-O-(5-chloro-2- thenyl)-2'-deoxy-5-fluorouridine in 50 ml of pyridine were added 0.72 g of N,N-diethyl-β-alanine hydrochloride and 1.61 g of triisopropylbenzenesulfonyl chloride, and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, and the residue was placed on silica gel column and eluted with 2% methanol-chloroform for purification, thereby giving 0.97 g of 3'-O-(5-chloro-2-thenyl)-2'-deoxy-5'-O- [3-(diethylamino)propanoyl]-5-fluorouridine 2,4,6-triisopropylbenzenesulfonate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washeluted with 2% methanol-chloroform for purification

Sources & evidence

ORD record
ord-987dc38f56dc4160bdbbf13e0e227e72
Source dataset
uspto-grants-1991_02
Patent number
US04992534

Reaction notes

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