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

HRID 1696995ノート

反応式

HRID 1696995 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

{(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+).

後処理

  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

出典と根拠

ORDレコード
ord-13651a05b63d4d0db8dc129024474195
出典データセット
uspto-grants-2012_04
特許番号
US08163754B2

反応ノート

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