Acetone → ((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol

HRID 552720ノート

反応式

HRID 552720 の反応式
[NH2:1][C:2]1[C:3]([NH:9][C@@H:10]2[CH2:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([OH:17])[C@H:11]2[OH:18])=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].O.[C:20]1(C)[CH:25]=CC(S(O)(=O)=O)=C[CH:21]=1.[CH3:31]OC(OC)OC.CC(C)=O.COC(OC)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:8][C:7]1[N:6]=[CH:5][N:4]=[C:3]2[C:2]=1[N:1]=[CH:31][N:9]2[C@H:10]1[C@@H:11]2[O:18][C:20]([CH3:25])([CH3:21])[O:17][C@@H:12]2[C@@H:13]([CH2:15][OH:16])[CH2:14]1

参加物

8

反応物 6

HCID 180AcetoneHCID 64952,2-DimethoxypropaneHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 10978690(1R,2S,3R,5R)-3-((5-amino-6-chloropyrimidin-4-yl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diol

生成物 1

HCID 10064860((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(1R,2S,3R,5R)-3-[(5-Amino-6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)cyclopentane-1,2-diol (335.0 mg, 0.001219 mol) and p-toluenesulfonic acid monohydrate (280 mg, 0.0015 mol) was dissolved in N,N-dimethylformamide (5.00 mL) and trimethoxymethane (10.0 mL, 0.0914 mol) under an atmosphere of nitrogen at 25° C. The reaction was stirred overnight, concentrated in vacuo, diluted with water and concentrated in vacuo again. The residue was then twice concentrated in vacuo from toluene. The residue was taken up in acetone (15.0 mL, 0.204 mol) and 2,2-dimethoxypropane (5.0 mL, 0.041 mol) and stirred for 2 hours, until complete by LCMS. The mixture was basified with sodium bicarbonate solution (20 mL), and concentrated in vacuo to remove organic solvent. The aqueous residue was extracted with DCM (4×20 mL) and the combined organic phase was concentrated in vacuo. Flash chromatography (0-100% EtOAc/DCM) gave the desired product (210 mg, 53%)

後処理

  1. customat 25° C
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. concentrationconcentrated in vacuo again
  5. concentrationThe residue was then twice concentrated in vacuo from toluene
  6. concentrationconcentrated in vacuo
  7. customto remove organic solvent
  8. extractionThe aqueous residue was extracted with DCM (4×20 mL)
  9. concentrationthe combined organic phase was concentrated in vacuo

出典と根拠

ORDレコード
ord-2c92fd814398425bbf4d9093eec58fca
出典データセット
uspto-grants-2011_05
特許番号
US07951810B2

反応ノート

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