Tetrabutylammonium Fluoride → Lamivudine

HRID 6424

반응식

HRID 6424 반응식
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

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 131718191HCID 131718191, 화합물

생성물 1

HCID 60825Lamivudine수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9dd9e53838e64349bfafd944e71e35ae
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248776

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