Acetic Acid → N-(2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)-N-(1-ethylpropyl)amine

HRID 2268414ノート

反応式

HRID 2268414 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH2:19][CH2:20][CH2:21][C:22]1[N:30]=[C:29]2[C:25]([N:26]=[CH:27][N:28]2[C@H:31]2[C@H:35]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C@H:34]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])[C@@H:33]([CH2:52][O:53][CH3:54])[O:32]2)=[C:24]([NH:55][CH2:56][CH:57]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[N:23]=1.[CH2:70]([C:72]([CH2:74][CH3:75])=O)[CH3:71]>ClCCl.C(OCC)(=O)C>[Si:37]([O:36][C@@H:35]1[C@H:34]([O:44][Si:45]([C:48]([CH3:49])([CH3:50])[CH3:51])([CH3:47])[CH3:46])[C@@H:33]([CH2:52][O:53][CH3:54])[O:32][C@H:31]1[N:28]1[CH:27]=[N:26][C:25]2[C:29]1=[N:30][C:22]([CH2:21][CH2:20][NH:19][CH:72]([CH2:74][CH3:75])[CH2:70][CH3:71])=[N:23][C:24]=2[NH:55][CH2:56][CH:57]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)([C:40]([CH3:41])([CH3:42])[CH3:43])([CH3:39])[CH3:38]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 7288Ethyl ketone2 回HCID 5049666Sodium triacetoxyborohydride2 回HCID 69534061N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine

生成物 1

HCID 69534102N-(2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)-N-(1-ethylpropyl)amine収率 91.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium triacetoxyborohydride (105 mg, 0.51 mmol) and glacial acetic acid (24 mg, 0.40 mmol) were added to a stirred solution of N-{2-(2-aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine (250 mg, 0.34 mmol) (preparation 18) and diethyl ketone (58 mg, 0.68 mmol) in dichloromethane (15 ml) and the resulting mixture stirred under an atmosphere of nitrogen gas at room temperature overnight. Additional portions of diethyl ketone (30 mg, 0.35 mmol) and sodium triacetoxyborohydride (60 mg, 0.29 mmol) were then added and stirring continued at room temperature for a further 24 hr. The mixture was diluted with ethyl acetate (20 ml) and washed sequentially with saturated aqueous sodium hydrogen carbonate solution, brine and water. The organic phase was separated and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4) to give the title compound (250 mg) as a gum. MS: 803 (MH+).

後処理

  1. stirringstirring
  2. waitcontinued at room temperature for a further 24 hr
  3. washwashed sequentially with saturated aqueous sodium hydrogen carbonate solution, brine and water
  4. customThe organic phase was separated
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4)

出典と根拠

ORDレコード
ord-76b3281e58304efb9171e3cb52836bd9
出典データセット
uspto-grants-2001_12
特許番号
US06326359B1

反応ノート

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