Tetrabutylammonium Fluoride → Lamivudine

HRID 6424

反応式

HRID 6424 の反応式
C([CH:5]([O:19][SiH](C1C=CC=CC=1)C1C=CC=CC=1)[C@H:6]1[S:10][CH2:9][C@@H:8]([N:11]2[CH:18]=[CH:17][C:15]([NH2:16])=[N:14][C:12]2=[O:13])[O:7]1)CCC.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:19][CH2:5][C@H:6]1[S:10][CH2:9][C@@H:8]([N:11]2[CH:18]=[CH:17][C:15]([NH2:16])=[N:14][C:12]2=[O:13])[O:7]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 131718191HCID 131718191、化合物

生成物 1

HCID 60825Lamivudine収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of the β anomer 17 (0.15 g, 0.32 mmol) in THF (25 mL) was added tetrabutylammonium fluoride 1M in THF (0.35 mL, 0.35 mmol, 1.1 eq) and the reaction was allowed to stir at room temperature until TLC indicated the disappearance of starting material (30 min). The reaction mixture was concentrated under reduced pressure and the residue purified by preparative TLC using 12% MeOH/CHCl3 as development solvent to give 0.055 g (75%) of 3 from ethyl ether/MeOH (trace) as a white crystalline solid. [α]23D =-121.6 (c 1.1, MeOH) (for the S,R isomer 2 [α]23D =120.96 (c 1.06, MeOH)); 1H NMR: ((CD3)2SO) δ 3.03 (dd, J5,4a =4.4 Hz, J4a,4b =11.86 Hz, 1 H, 4a-H), 3.43 (dd, J5,4b =5.3 Hz, J4a,4b =11.86 Hz, 1 H, 4b-H), 3.80 (app t on D2O exchange goes to d, J2,2-CH2-OR =4.17 Hz, 2 H, 2-CH2 -OH), 5.27 (t, J2-CH2,OH =4.6 Hz, 1 H, 2-CH2OH), 5.22 (t, J2,2-CH2-OH =4.17 Hz, 1 H, 2-H), 5.88 (d, J5,6 =7.47 Hz, 1 H, H-5), 6.21 (app t, J=5.05 and 4.84 Hz, 1 H, 5-H), 7.19 (bs, 2 H, NH2), 7.89 (d, J5,6 =7.47 Hz, 1 H, H-6).

後処理

  1. customthe disappearance of starting material (30 min)
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue purified by preparative TLC

出典と根拠

ORDレコード
ord-9dd9e53838e64349bfafd944e71e35ae
出典データセット
uspto-grants-1993_09
特許番号
US05248776

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