Sodium Carbonate → N-{2-[Cyclopentyl(isopropyl)amino]ethyl}-N'-({6-[(2,2-diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-9H-purin-2-yl}methyl)urea

HRID 1168277노트

반응식

HRID 1168277 반응식
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([CH2:45][NH:46][C:47]([NH:49][CH2:50][CH2:51][N:52]([CH:56]1[CH2:60][CH2:59][CH2:58][CH2:57]1)[CH:53]([CH3:55])[CH3:54])=[O:48])=[N:25][C:26]=2[NH:30][CH2:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH:56]1([N:52]([CH:53]([CH3:54])[CH3:55])[CH2:51][CH2:50][NH:49][C:47]([NH:46][CH2:45][C:24]2[N:23]=[C:22]3[C:27]([N:28]=[CH:29][N:21]3[C@H:6]3[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]4[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=4)[O:7]3)=[C:26]([NH:30][CH2:31][CH:32]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:25]=2)=[O:48])[CH2:57][CH2:58][CH2:59][CH2:60]1

참가 물질

4

반응물 2

HCID 10340Sodium CarbonateHCID 69978470(2R,3R,4R,5R)-4-(Acetoxy)-2-{2-({[({2-[cyclopentyl(isopropyl)-amino]ethyl}amino)carbonyl]amino}methyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl Acetate

생성물 1

HCID 10305826N-{2-[Cyclopentyl(isopropyl)amino]ethyl}-N'-({6-[(2,2-diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-9H-purin-2-yl}methyl)urea수율 29.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of (2R,3R,4R,5R)-4-(acetoxy)-2-{2-({[({2-[cyclopentyl(isopropyl)amino]ethyl}amino)carbonyl]amino}methyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate (Preparation 45) (135 mg, 0.16 mmol) and sodium carbonate (5 mg, 0.05 mmol) in methanol (5 ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:conc. aqueous ammonia (95:5:0.5 by volume) gradually changing to dichloromethane:methanol:conc. aqueous ammonia (90:10:1 by volume). Product containing fractions were evaporated and the resulting solid was dried under vacuum to afford the title compound as a white powder (35 mg).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
  3. additionProduct containing fractions
  4. customwere evaporated
  5. customthe resulting solid was dried under vacuum

출처 및 근거

ORD 기록
ord-ca367d2964cf4325b7d696f35d7fe974
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06624158B2

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