Triethylamine → N(6)-Methyl-N(6)-cyclohex-3-enylmethyl-adenosine

HRID 328195ノート

反応式

HRID 328195 の反応式
C([N:4]1[C:12]2[CH:7]([N:8](C(=O)C)[CH2:9][N:10](C(=O)C)[C:11]=2Cl)[N:6]([C@@H:20]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]2[OH:22])[CH2:5]1)(=O)C.CN([CH:32]1[CH2:37][CH2:36][CH:35]=[CH:34][CH2:33]1)C.[CH2:38]([N:40](CC)[CH2:41]C)C>C(O)CCC>[CH3:38][N:40]([CH2:41][CH:32]1[CH2:37][CH2:36][CH:35]=[CH:34][CH2:33]1)[C:11]1[C:12]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[CH:9][N:10]=1)[C@@H:20]1[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]1[OH:22]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 21444275Methyl-cyclohex-3-enyl-methylamineHCID 131710375Triacetyl-6-chloro-9-(beta-D-ribofuranosyl)-purine

生成物 1

HCID 22796829N(6)-Methyl-N(6)-cyclohex-3-enylmethyl-adenosine

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

6.2 g. triacetyl-6-chloro-9-(β-D-ribofuranosyl)-purine, 2.5 g. methyl-cyclohex-3-enyl-methylamine and 2.8 ml. triethylamine were left to stand at ambient temperature for 16 hours in 100 ml. butanol. The reaction mixture was then mixed with 150 ml. diethyl ether, extracted twice with water and the organic phase evaporated to dryness in a vacuum. The residue was dissolved in 100 ml. 25% methanolic ammonia and left to stand for a few days at ambient temperature. 3.4 g. (60% of theory) N(6)-methyl-N(6)-cyclohex-3-enyl-methyl-adenosine crystallized out directly from the methanolic solution; m.p. 154°- 156° C.

後処理

  1. additionThe reaction mixture was then mixed with 150 ml
  2. extractiondiethyl ether, extracted twice with water
  3. customthe organic phase evaporated to dryness in a vacuum
  4. dissolutionThe residue was dissolved in 100 ml
  5. wait25% methanolic ammonia and left
  6. waitto stand for a few days at ambient temperature
  7. custom(60% of theory) N(6)-methyl-N(6)-cyclohex-3-enyl-methyl-adenosine crystallized out directly from the methanolic solution

出典と根拠

ORDレコード
ord-cf50b2e48ad24d0b8db40ab3fd41b9bc
出典データセット
uspto-grants-1977_04
特許番号
US04016262

反応ノート

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