Potassium Carbonate → Methyl [6-(benzyloxy)-9H-purin-9-yl]acetate

HRID 400332ノート

反応式

HRID 400332 の反応式
[CH2:1]([O:8][C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[NH:11][CH:12]=[N:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26](=[O:29])[CH2:27]Br>CN(C=O)C.C(O)CCC.C(O)(=O)C.O>[CH2:1]([O:8][C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[CH2:27][C:26]([O:25][CH3:24])=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 8536776-Benzyloxypurine

生成物 1

HCID 59289995Methyl [6-(benzyloxy)-9H-purin-9-yl]acetate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 22056973Butanol acetic acid water溶媒

実験手順

6-Benzyloxypurine (4.18 g; 18.5 mmol) was added to a suspension of potassium carbonate (3.1 g; 22.4 mmol) in DMF (100 ml). After 15 min., bromoacetic acid methyl ester (1.93 ml; 20.4 mmol) was added. The reaction was monitored by TLC in butanol:acetic acid:water 4:1:1. Upon completion, the reaction mixture was partitioned between water (600 ml) and ethyl acetate (600 ml). The organic phase was dried over magnesium sulfate and evaporated to a volume of ˜10 ml and precipitated with pet. ether. The two products were separated by column chromatography using ethyl acetate as the solvent. The products were precipitated in pet. ether. Yield: 2.36 g (43%). Melting point: 111.5-115° C. UV λmax=250 nm (9-alkylated); λmax=260 nm (7-alkylated). 1H-NMR (DMSO-d6): 8.60 (1H, s); 8.43 (1H, s); 7.6-7.35 (5H, m); 5.69 (2H, s); 5.26 (2H, s); 3.75 (3H, s).

後処理

  1. customUpon completion, the reaction mixture was partitioned between water (600 ml) and ethyl acetate (600 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated to a volume of ˜10 ml
  4. customprecipitated with pet. ether
  5. customThe two products were separated by column chromatography
  6. customThe products were precipitated in pet. ether

出典と根拠

ORDレコード
ord-d9b33f15ebec4ecd96476e366eafab89
出典データセット
uspto-grants-2014_06
特許番号
US08741566B2

反応ノート

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