Chlorotrimethylsilane → HCID 22874774, 화합물

HRID 264742노트

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HRID 264742 반응식
[CH2:1]([O:4][C@@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C@H:6]1[N:13]1[CH:20]=[CH:19][C:17]([NH2:18])=[N:16][C:14]1=[O:15])[CH2:2][CH3:3].C[Si](Cl)(C)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[NH4+].[OH-]>O.N1C=CC=CC=1>[C:26]([NH:18][C:17]1[CH:19]=[CH:20][N:13]([C@@H:6]2[O:7][C@H:8]([CH2:11][OH:12])[C@@H:9]([OH:10])[C@H:5]2[O:4][CH2:1][CH2:2][CH3:3])[C:14](=[O:15])[N:16]=1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

7

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 14923Ammonium HydroxideHCID 228747462'-O-Propylcytidine2회

생성물 1

HCID 22874774HCID 22874774, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

To the 2'-O-propylcytidine reaction mixture of Example 82 in an ice bath was added pyridine (60 ml) and trimethylsilyl chloride (60 ml). The reaction was stirred for 30 mins followed by the addition of benzoyl chloride (55 ml). The resulting reaction mixture was stirred for 2.5 hrs and then cooled in an ice bath. H2O (100 ml) and conc. NH4OH (100 ml) were added. After stirring for 30 mins, the reaction mixture was evaporated and the residue partition between H2O and CH2Cl2. The organic phase was washed once with dil Na2CO3, once with dil HCl, dried over MgSO4 and evaporated. The resulting residue was loaded on a silica gel column (150 g) and eluted with first CH2Cl2 then 5 to 10% MeOH in CH2Cl2 as the elution solvent. The product containing fractions were evaporated to a foam. The foam was crystallized from EtOAc/Hexanes to give the product (6.5 g total) in several crystal batches.

후처리

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 2.5 hrs
  3. temperaturecooled in an ice bath
  4. stirringAfter stirring for 30 mins
  5. customthe reaction mixture was evaporated
  6. customthe residue partition between H2O and CH2Cl2
  7. washThe organic phase was washed once with dil Na2CO3, once with dil HCl
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. washeluted with first CH2Cl2
  11. additionThe product containing fractions
  12. customwere evaporated to a foam
  13. customThe foam was crystallized from EtOAc/Hexanes
  14. customto give the product (6.5 g total) in several crystal batches

출처 및 근거

ORD 기록
ord-a52d256f69104e05915b7e8659449b62
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646265

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