Water → Posaconazole Impurity 326

HRID 512818ノート

反応式

HRID 512818 の反応式
[OH-].[Na+].O.[CH2:4]([O:11][C@H:12]([C@@H:14]([N:17]1[C:21](=[O:22])[N:20]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][N:32]([C:35]4[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=4)[CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[CH:19]=[N:18]1)[CH2:15][CH3:16])[CH3:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CC1C=CC(S(O[CH2:53][C@H:54]2[CH2:58][C@:57]([CH2:67][N:68]3[CH:72]=[N:71][CH:70]=[N:69]3)([C:59]3[CH:64]=[CH:63][C:62]([F:65])=[CH:61][C:60]=3[F:66])[O:56][CH2:55]2)(=O)=O)=CC=1>CS(C)=O>[N:68]1([CH2:67][C@@:57]2([C:59]3[CH:64]=[CH:63][C:62]([F:65])=[CH:61][C:60]=3[F:66])[O:56][CH2:55][C@@H:54]([CH2:53][O:41][C:38]3[CH:39]=[CH:40][C:35]([N:32]4[CH2:31][CH2:30][N:29]([C:26]5[CH:27]=[CH:28][C:23]([N:20]6[C:21](=[O:22])[N:17]([C@H:14]([CH2:15][CH3:16])[C@@H:12]([O:11][CH2:4][C:5]7[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=7)[CH3:13])[N:18]=[CH:19]6)=[CH:24][CH:25]=5)[CH2:34][CH2:33]4)=[CH:36][CH:37]=3)[CH2:58]2)[CH:72]=[N:71][CH:70]=[N:69]1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 108956292,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-((((4-methylphenyl)sulfonyl)oxy)methyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitolHCID 462232972-((1S,2S)-1-Ethyl-2-(phenylmethoxy)propyl)-2,4-dihydro-4-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)-3H-1,2,4-triazol-3-one

生成物 1

HCID 89463936Posaconazole Impurity 326

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
52.5 °C

実験手順

A solution of sodium hydroxide (9.2 g) and water (10 ml) was cooled to 25-35° C. and added dimethyl sulfoxide (350 ml), followed by 1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (50 gms) compound of formula-20 at 25-35° C. The reaction mixture was stirred for 45 minutes at the same temperature. ((3S,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluoro phenyl)tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate (50 μms) compound of formula-10 was added to the above reaction mixture and heated to 45-60° C. The reaction mixture was stirred for 6 hours at the same temperature. After completion of the reaction, the reaction mixture was quenched with water and neutralized with hydrochloric acid. The reaction mixture was stirred for 1 hour at 25-35° C. Filtered the solid and washed with water. Dried the solid to get the title compound. Yield: 79 g

後処理

  1. customformula-20 at 25-35° C
  2. stirringThe reaction mixture was stirred for 6 hours at the same temperature
  3. customAfter completion of the reaction
  4. customthe reaction mixture was quenched with water and neutralized with hydrochloric acid
  5. stirringThe reaction mixture was stirred for 1 hour at 25-35° C
  6. filtrationFiltered the solid
  7. washwashed with water
  8. customDried the solid

出典と根拠

ORDレコード
ord-4ec8a7fecbff4859a859f8772d40dc2a
出典データセット
uspto-grants-2015_08
特許番号
US09102664B2

反応ノート

読み込み中…