Trifluoroacetic acid → N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

HRID 1696995노트

반응식

HRID 1696995 반응식
C(OC(=O)[N:7]([C@H:12]1[CH2:16][C@@H:15]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([Cl:32])=[N:21][C:22]=3[NH:26][CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[C@H:14]([OH:33])[C@@H:13]1[OH:34])[C:8](=[O:11])[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:32][C:20]1[N:19]=[C:18]2[C:23]([N:24]=[CH:25][N:17]2[C@@H:15]2[CH2:16][C@H:12]([NH:7][C:8](=[O:11])[CH2:9][CH3:10])[C@@H:13]([OH:34])[C@H:14]2[OH:33])=[C:22]([NH:26][CH:27]([CH2:28][CH3:29])[CH2:30][CH3:31])[N:21]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86622635{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionyl-carbamic acid tert-butyl ester

생성물 1

HCID 11647233N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionyl-carbamic acid tert-butyl ester (300 mg, 0.59 mmol) is dissolved in dichloromethane (5 ml). TFA (2 ml) is added and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by LCMS after 1 hour. The solvent is removed in vacuo and the residue is partitioned between dichloromethane (50 ml) and saturated NaHCO3 (50 ml). The organic layer is washed with water (20 ml) and brine (20 ml), dried over MgSO4, filtered and the solvent is removed in vacuo to give the title compound. 1H nmr (MeOD, 400 MHz); 8.05(s, 1H), 4.75(m, 1H), 4.60(m, 1H), 4.20(m, 2H), 4.00(m, 1H), 2.90(m, 1H), 2.40(q, 2H), 2.10(m, 1H), 1.70(m, 2H), 1.60(m, 2H), 1.20(t, 3H), 0.95(t, 6H), MS (ES+) mine 411 (MH+).

후처리

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between dichloromethane (50 ml) and saturated NaHCO3 (50 ml)
  3. washThe organic layer is washed with water (20 ml) and brine (20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-13651a05b63d4d0db8dc129024474195
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163754B2

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