Propionyl chloride → N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide

HRID 1696990ノート

反応式

HRID 1696990 の反応式
FC(F)(F)C(O)=O.[NH2:8][C@H:9]1[CH2:13][C@@H:12]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([Cl:38])=[N:18][C:19]=3[NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:11]([OH:39])[C@@H:10]1[OH:40].C(N(C(C)C)CC)(C)C.[C:50](Cl)(=[O:53])[CH2:51][CH3:52]>C1COCC1>[Cl:38][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@@H:12]2[CH2:13][C@H:9]([NH:8][C:50](=[O:53])[CH2:51][CH3:52])[C@@H:10]([OH:40])[C@H:11]2[OH:39])=[C:19]([NH:23][CH2:24][CH:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:18]=1

参加物

5

反応物 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 86622631(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol trifluoroacetate

生成物 1

HCID 86622630N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol trifluoroacetate (9.50 g, 16.42 mmol) and diisopropylethylamine (6.36 g, 49.27 mmol) are placed in a flask with dry THF (150 ml). Propionyl chloride (1.52 g, 16.42 mmol) is added dropwise 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 (250 ml) and water (250 ml). The organic layer is washed with water (200 ml) and brine (200 ml), dried over MgSO4, filtered and the solvent is removed in vacuo. The solid is recrystallised from 1,2-dichloroethane to give the title compound. 1H nmr (MeOD, 400 MHz); 8.00(s, 1H), 7.40-7.15(m, 10H), 4.75(m, 1H), 4.60(m, 1H), 4.50(m, 1H), 4.20(m, 3H), 3.95(m, 1H), 2.85(m, 1H), 2.40(q, 2H), 2.10(m, 1H), 1.20(t, 3H), MS (ES+) m/e 521 (MH+).

後処理

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between dichloromethane (250 ml) and water (250 ml)
  3. washThe organic layer is washed with water (200 ml) and brine (200 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe solid is recrystallised from 1,2-dichloroethane

出典と根拠

ORDレコード
ord-128c723975a04bb8bf491be2dfc25cab
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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