Sodium Bicarbonate → HCID 11231258, 화합물

HRID 1836208노트

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HRID 1836208 반응식
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3O)[C:6]=2[N:7]=1.O.CC#N.[C:25](OC(C)(C)C(Br)=O)(=[O:27])C.C([O-])(O)=O.[Na+]>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([O:27][CH3:25])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@H:14]4[O:15][C@@H:12]34)[C:6]=2[N:7]=1

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 27247151-Bromocarbonyl-1-methylethyl acetateHCID 11174104HCID 11174104, 화합물HCID 18373917Acetonitrile--water (1/1)

생성물 1

HCID 11231258HCID 11231258, 화합물수율 115%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of 2-amino-7-(β-D-ribofuranosyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.8 g, 6.0 mmol) in acetonitrile (80 mL) were added a solution of H2O/CH3CN (1:9, 1.08 mL) and then α-acetoxyisobutyryl bromide (3.5 mL, 24 mmol). After 2 h stirring at room temperature, saturated aqueous NaHCO3 (170 mL) was added and the mixture was extracted with EtOAc (300+200 mL). The combined organic phase was washed with brine (100 mL), dried (Na2SO4) and evaporated to a pale yellow foamy residue. This was suspended in anhydrous MeOH (80 mL) and stirred overnight with 25 mL of DOWEX OH resin (previously washed with anhydrous MeOH). The resin was filtered, washed thoroughly with MeOH and the combined filtrate evaporated to give a pale yellow foam (1.92 g).

후처리

  1. extractionthe mixture was extracted with EtOAc (300+200 mL)
  2. washThe combined organic phase was washed with brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to a pale yellow foamy residue
  5. stirringstirred overnight with 25 mL of DOWEX OH resin (
  6. washpreviously washed with anhydrous MeOH)
  7. filtrationThe resin was filtered
  8. washwashed thoroughly with MeOH
  9. customthe combined filtrate evaporated

출처 및 근거

ORD 기록
ord-424aa4319ca14bd9a899b6268c7dafc6
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777395B2

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