Hexane → HCID 178519959、化合物

HRID 2169397ノート

反応式

HRID 2169397 の反応式
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:45]1[CH2:48][O:47][CH2:46]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH:45]1[CH2:46][O:47][CH2:48]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[CH2:31][CH2:32][CH2:33][CH2:34]2)[N:15]=1)=[O:13]

参加物

6

反応物 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 178455271HCID 178455271、化合物

生成物 1

HCID 178519959HCID 178519959、化合物収率 73.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-oxetan-3-yl-amide (362) (290 mg, 0.43 mmol) in tetrahydrofuran (10 mL) was added tetrabutylammoniumfluorid (1M in tetrahydrofuran, 1.3 mL, 13 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 1.5 h (silica TLC, ethyl acetate:hexane=1:1/SiO2/UV, Rf=0.3.) The tetrahydrofuran was removed in vacuum and the crude mass was diluted with ethyl acetate (50 mL) and washed with water (25 mL) and brine (25 mL). The organic phase was thereafter dried and concentrated in vacuum to get a crude mass which was purified by CombiFlash using a gradient eluent mixture of ethyl acetate and hexane to obtain pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-oxetan-3-yl-amide (363) (175 mg, 73%) as a white solid.

後処理

  1. customwas removed in vacuum
  2. additionthe crude mass was diluted with ethyl acetate (50 mL)
  3. washwashed with water (25 mL) and brine (25 mL)
  4. customThe organic phase was thereafter dried
  5. concentrationconcentrated in vacuum
  6. customto get a crude mass which
  7. customwas purified by CombiFlash
  8. additiona gradient eluent mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-f54893f6170e48a392a83c725a32920f
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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