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Dimethylformamide → tert-butyl 2-[(1R)-1-({[(6R)-6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-yl]carbonyl}amino)propyl]isonicotinate

HRID 80579
ノート
印刷プレビュー

反応式

HRID 80579 の反応式
C([C@H]([C@@H](C(O)=O)O)O)(O)=O.[NH2:11][C@@H:12]([C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][N:27]=1)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH3:14].CN(C)C=O.C(N(CC)CC)C.[Cl:40][C:41]1[CH:42]=[CH:43][C:44]([O:80][CH3:81])=[C:45]([CH:79]=1)[CH2:46][C@H:47]1[C:53](=[O:54])[N:52]([C:55](OC2C=CC=CC=2Cl)=[O:56])[CH2:51][C:50](=[O:65])[N:49]([CH2:66][C:67]2[C:72]([O:73][CH3:74])=[CH:71][C:70]([O:75][CH3:76])=[CH:69][C:68]=2[O:77][CH3:78])[CH2:48]1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:40][C:41]1[CH:42]=[CH:43][C:44]([O:80][CH3:81])=[C:45]([CH:79]=1)[CH2:46][C@H:47]1[C:53](=[O:54])[N:52]([C:55]([NH:11][C@@H:12]([C:15]2[CH:16]=[C:17]([CH:25]=[CH:26][N:27]=2)[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:13][CH3:14])=[O:56])[CH2:51][C:50](=[O:65])[N:49]([CH2:66][C:67]2[C:68]([O:77][CH3:78])=[CH:69][C:70]([O:75][CH3:76])=[CH:71][C:72]=2[O:73][CH3:74])[CH2:48]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66935304(6R)-2-chlorophenyl 6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-carboxylateHCID 66935362tert-butyl 2-[(1R)-1-aminopropyl]-isonicotinate D-tartrate

生成物 1

HCID 70815243
tert-butyl 2-[(1R)-1-({[(6R)-6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-yl]carbonyl}amino)propyl]isonicotinate
収率 71.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒

実験手順

To the compound 5105 described in WO 06-059801A, that is, tert-butyl 2-[(1R)-1-aminopropyl]-isonicotinate D-tartrate (157 mg) in an N,N-dimethylformamide (1.5 ml) solution, triethylamine (0.113 ml) was added under ice cooling, and the mixture was stirred at that temperature for 5 minutes. To the reaction solution, the compound S141C described in WO 06-059801A, that is, (6R)-2-chlorophenyl 6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepane-1-carboxylate (250 mg) and 4-dimethylaminopyridine (49 mg) were added, and the mixture was stirred at 0° C. for 18 hours. The reaction solution was diluted with ethyl acetate, then was successively washed with saturated aqueous ammonium chloride solution and brine. The organic layer was dried over anhydrous sodium sulfate, then was concentrated. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=1/1 to 1/2) to obtain tert-butyl 2-[(1R)-1-({[(6R)-6-(5-chloro-2-methoxybenzyl)-3,7-dioxo-4-(2,4,6-trimethoxybenzyl)-1,4-diazepan-1-yl]carbonyl}amino)propyl]isonicotinate (compound S39a) (210 mg).

後処理

  1. stirringthe mixture was stirred at 0° C. for 18 hours
  2. washwas successively washed with saturated aqueous ammonium chloride solution and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationwas concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=1/1 to 1/2)

出典と根拠

ORDレコード
ord-6cd33210deed409195bf59353f72167e
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846660B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート