Oxalyl chloride → HCID 6475156, 화합물

HRID 1939863노트

반응식

HRID 1939863 반응식
[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]

참가 물질

7

반응물 3

HCID 65578Oxalyl chlorideHCID 15460476HCID 15460476, 화합물HCID 54253886HCID 54253886, 화합물

생성물 1

HCID 6475156HCID 6475156, 화합물수율 70.7%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6228Dimethylformamide용매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0a7cbab9d9784085930b52325b986db8
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05698532

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