Thymine → N-Benzyl-N-[2-(thymin-1-yl) ethyl]-glycine tert-butyl ester

HRID 54614Notes

Reaction equation

HRID 54614 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][CH2:10]OS(C)(=O)=O)([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH:32]=[C:30]([CH3:31])[C:28](=[O:29])[NH:27][C:25]1=[O:26].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CN(C)C=O.C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[CH2:7][N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][CH2:10][N:24]1[CH:32]=[C:30]([CH3:31])[C:28](=[O:29])[NH:27][C:25]1=[O:26])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1135ThymineHCID 1140TolueneHCID 11430Potassium CarbonateHCID 15817340N-Benzyl-N-[2-(methanesulphonyloxy)ethyl]-glycine tert-butyl ester

Product 1

HCID 15817341N-Benzyl-N-[2-(thymin-1-yl) ethyl]-glycine tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 2 (10.73 g; 31 mmol), thymine (7.88 g; 62 mmol) and potassium carbonate (8.64 g; 62 mmol) are suspended in anhydrous N,N-dimethylformamide (325 ml). The suspension is stirred at room temperature for 1 h and then at 80° C. for 6 h. The cooled mixture is codistilled repeatedly with toluene, and the residue is taken up in chloroform (500 ml) and extracted twice with water (150 ml on each occasion). The crude product is purified by chromatography on silica gel (eluent: toluene/ethanol, 27:1). Yield: 5.58 g (48%).

Workup

  1. waitat 80° C. for 6 h
  2. extractionextracted twice with water (150 ml on each occasion)
  3. customThe crude product is purified by chromatography on silica gel (eluent: toluene/ethanol, 27:1)

Sources & evidence

ORD record
ord-0ca30cdc59ad47919c0f0e05bc51684c
Source dataset
uspto-grants-1997_04
Patent number
US05623049

Reaction notes

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