Diethyl Ether → Isohexane ethyl acetate

HRID 131582ノート

反応式

HRID 131582 の反応式
C(Cl)(=[O:3])C.OC1CON(C([C:13]2[C:21]3[C:20](=[O:22])[N:19](C)[C:18](=[O:24])[N:17]([CH:25]([CH3:27])[CH3:26])[C:16]=3[S:15][C:14]=2[CH2:28]C2C3C(=NC=CC=3)NC=2)=O)C1.[CH3:38][CH2:39][O:40][CH2:41][CH3:42]>C1(C)C=CC=CC=1.[Ag]OC#N>[CH3:28][CH2:14][CH2:13][CH:21]([CH3:20])[CH3:16].[C:39]([O:40][CH2:41][CH3:42])(=[O:3])[CH3:38].[CH3:13][C:14]1[S:15][C:16]2[N:17]([CH:25]([CH3:27])[CH3:26])[C:18](=[O:24])[NH:19][C:20](=[O:22])[C:21]=2[C:42]=1[C:41]([O:40][CH3:39])=[O:3]

参加物

7

反応物 3

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 688045155-[[4-Hydroxyisoxazolidin-2-yl]carbonyl]-3-methyl-1-(1-methylethyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

生成物 2

HCID 21882781Isohexane ethyl acetateHCID 131726917Methyl 1-isopropyl-6-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

試薬・触媒・溶媒 2

HCID 178513473HCID 178513473、化合物触媒HCID 1140Toluene溶媒2 回

実験手順

Silver cyanate (13.5 g) suspended in anhydrous toluene (90 ml) under nitrogen was treated dropwise with acetyl chloride (5.34 ml) and stirred vigorously for 30 min. The product of example 8 step a) (23 g) dissolved in anhydrous toluene (15 ml) was added and the mixture was stirred for 72 h. Ether (360 ml) was added and the insoluble material was filtered off and washed with a small volume of ether. The combined organic solutions were washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was treated with a solution of sodium methoxide in methanol (25 wt %, 64 ml) at room temperature for 72 h. The reaction was cooled in ice and treated with trimethylsilyl chloride (50.8 ml) and stirred at room temperature overnight. All volatiles were removed in vacuo and the residue partitioned between water and ethyl acetate. Drying and evaporation of the organic solution left a residue, which was chromatographed (SiO2/2:1 isohexane-ethyl acetate then 3:2 isohexane-ethyl acetate) to isolate the sub-title compound(12.2 g). MS(ES) 283 [M+H]+

後処理

  1. additionwas added
  2. stirringthe mixture was stirred for 72 h
  3. filtrationthe insoluble material was filtered off
  4. washwashed with a small volume of ether
  5. washThe combined organic solutions were washed with saturated sodium bicarbonate solution
  6. customdried
  7. customevaporated
  8. additionThe residue was treated with a solution of sodium methoxide in methanol (25 wt %, 64 ml) at room temperature for 72 h
  9. temperatureThe reaction was cooled in ice
  10. additiontreated with trimethylsilyl chloride (50.8 ml)
  11. stirringstirred at room temperature overnight
  12. customAll volatiles were removed in vacuo
  13. customthe residue partitioned between water and ethyl acetate
  14. customDrying
  15. customevaporation of the organic solution
  16. waitleft a residue, which
  17. customwas chromatographed (SiO2/2:1 isohexane-ethyl acetate

出典と根拠

ORDレコード
ord-1b25152494ac480cb4120c30b8159ae6
出典データセット
uspto-grants-2008_06
特許番号
US07384950B2

反応ノート

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