Hydrochloric Acid → 3-(3-(cyclobutyl(((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)amino)cyclobutyl)propanoic acid

HRID 511650ノート

反応式

HRID 511650 の反応式
O.[OH-].[Li+].[CH:4]1([N:8]([CH2:20][C@@H:21]2[C@@H:28]3[C@@H:24]([O:25][C:26]([CH3:30])([CH3:29])[O:27]3)[C@H:23]([N:31]3[C:35]4[N:36]=[CH:37][N:38]=[C:39]([NH:40][CH2:41][C:42]5[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:43]=5[O:50][CH3:51])[C:34]=4[CH:33]=[CH:32]3)[CH2:22]2)[CH:9]2[CH2:12][CH:11]([CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH2:10]2)[CH2:7][CH2:6][CH2:5]1.O1CCCC1.CO.Cl>>[CH:4]1([N:8]([CH2:20][C@@H:21]2[C@@H:28]3[C@@H:24]([O:25][C:26]([CH3:29])([CH3:30])[O:27]3)[C@H:23]([N:31]3[C:35]4[N:36]=[CH:37][N:38]=[C:39]([NH:40][CH2:41][C:42]5[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:43]=5[O:50][CH3:51])[C:34]=4[CH:33]=[CH:32]3)[CH2:22]2)[CH:9]2[CH2:10][CH:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:12]2)[CH2:7][CH2:6][CH2:5]1

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67775683ethyl 3-(3-(cyclobutyl(((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)amino)cyclobutyl)propanoate

生成物 1

HCID 677774823-(3-(cyclobutyl(((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)amino)cyclobutyl)propanoic acid

実験手順

Lithium hydroxide monohydrate (0.58 g, 14 mmol) added to a solution of ethyl 3-(3-(cyclobutyl(((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)amino)cyclobutyl)propanoate (0.91 g, 1.4 mmol) in Tetrahydrofuran (12 ml, 150 mmol) and Methanol (3 ml, 60 mmol). The reaction mixture was stirred overnight at RT, upon which it was acidified with 1 N HCl to pH=6. The volatiles were removed in vacuo and the remaining water removed by azeotropic distillation with ethanol followed by 18 hours on lyophilizer. The resulting off white solid was used without further purification.

後処理

  1. customThe volatiles were removed in vacuo
  2. customthe remaining water removed by azeotropic distillation with ethanol
  3. waitfollowed by 18 hours on lyophilizer
  4. customThe resulting off white solid was used without further purification

出典と根拠

ORDレコード
ord-9190451d96244855b0ebb29ddb600372
出典データセット
uspto-grants-2015_08
特許番号
US09096634B2

反応ノート

読み込み中…