Oxalyl chloride → HCID 6475156、化合物

HRID 1939863ノート

反応式

HRID 1939863 の反応式
[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH3:16])=[CH:10][C:3]=1[O:4][C@@H:5]([CH3:9])[C:6]([OH:8])=O.C(Cl)(=O)C(Cl)=O.[NH2:23][CH2:24][C@H:25]1[O:29][C@@H:28]([N:30]2[CH:37]=[C:36]([CH2:38][CH3:39])[C:34](=[O:35])[NH:33][C:31]2=[O:32])[C@@H:27]([F:40])[C@@H:26]1[OH:41]>C1(C)C=CC=CC=1.CN(C)C=O.[OH-].[Na+]>[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH3:16])=[CH:10][C:3]=1[O:4][C@@H:5]([CH3:9])[C:6]([NH:23][CH2:24][C@H:25]1[O:29][C@@H:28]([N:30]2[CH:37]=[C:36]([CH2:38][CH3:39])[C:34](=[O:35])[NH:33][C:31]2=[O:32])[C@@H:27]([F:40])[C@@H:26]1[OH:41])=[O:8]

参加物

7

反応物 3

HCID 65578Oxalyl chlorideHCID 15460476HCID 15460476、化合物HCID 54253886HCID 54253886、化合物

生成物 1

HCID 6475156HCID 6475156、化合物収率 70.7%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

24.2 g (0.091 mol) of (S)-2-(2,4-dichloro-5-methoxyphenoxy)-propionic acid were suspended in a mixture of 150 ml of toluene and 0.5 ml of dimethylformamide and the suspension was stirred under nitrogen. 15.0 ml (0.17 mol) of oxalyl chloride were added, with vigorous evolution of gas occurring. The mixture was stirred for 1 hour to give a homogeneous solution. The solvents were removed by evaporation, the residue was taken up in 100 ml of diethyl ether and the solution was added to a solution of 24.6 g (0.090 mol) of 1-(5-amino-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil in 290 ml of 0.31M sodium hydroxide solution. The heterogeneous mixture was shaken vigorously for 10 minutes to give a white precipitate which was filtered off and washed firstly with water and then with diethyl ether. The crude product was recrystallized from hot methanol to give 33.1 g (69.7%) of 1-[5-[2(S)-(2,4-dichloro-5-methoxyphenoxy)propionamido]-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl]-5-ethyluracil as a white crystalline solid, m.p. 195°-196° C.

後処理

  1. stirringThe mixture was stirred for 1 hour
  2. customto give a homogeneous solution
  3. customThe solvents were removed by evaporation
  4. stirringThe heterogeneous mixture was shaken vigorously for 10 minutes
  5. customto give a white precipitate which
  6. filtrationwas filtered off
  7. washwashed firstly with water
  8. customThe crude product was recrystallized from hot methanol

出典と根拠

ORDレコード
ord-0a7cbab9d9784085930b52325b986db8
出典データセット
uspto-grants-1997_12
特許番号
US05698532

反応ノート

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