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Acetic Acid → (R)-6-[[3-[[8-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944957
ノート
印刷プレビュー

反応式

HRID 1944957 の反応式
C(O)(=O)C.[NH2:5][CH2:6][C@@H:7]([C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:27])[NH:21]2)[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([NH:36][C:37]2[C:46]3[C:41](=[C:42]([CH3:68])[CH:43]=[C:44]([S:47]([C:50]4[CH:55]=[CH:54][CH:53]=[C:52]([C:56](=[O:67])[NH:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH:65]=O)[CH:51]=4)(=[O:49])=[O:48])[CH:45]=3)[N:40]=[CH:39][C:38]=2[C:69]([NH2:71])=[O:70])[CH:33]=[CH:34][CH:35]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[Si:9]([O:8][C@H:7]([C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:27])[NH:21]2)[CH2:6][NH:5][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][NH:57][C:56]([C:52]1[CH:51]=[C:50]([S:47]([C:44]2[CH:45]=[C:46]3[C:41](=[C:42]([CH3:68])[CH:43]=2)[N:40]=[CH:39][C:38]([C:69]([NH2:71])=[O:70])=[C:37]3[NH:36][C:32]2[CH:33]=[CH:34][CH:35]=[C:30]([O:29][CH3:28])[CH:31]=2)(=[O:48])=[O:49])[CH:55]=[CH:54][CH:53]=1)=[O:67])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]
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 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-oneHCID 866590914-[(3-Methoxyphenyl)amino]-8-methyl-6-[[3-[(8-oxooctyl)carbamoyl]phenyl]sulfonyl]quinoline-3-carboxamide

生成物 1

HCID 86659116
(R)-6-[[3-[[8-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide
収率 91.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Glacial acetic acid (0.005 mL, 0.089 mmol) and Intermediate 2 (50 mg, 0.149 mmol) were added to a stirring solution of Intermediate 112 (55 mg, 0.089 mmol) in DMF (2 mL) at rt. The resulting solution was stirred for 3 h, then NaBH(OAc)3 (57 mg, 0.267 mmol) was added in portions. The reaction mixture was stirred over night then poured into said. NaHCO3 (40 mL). The precipitate was filtered, washed with H2O (50 mL), and dried to give the title compound (76 mg) as a yellow solid. The compound was used with no further purification. ES/MS calcd. for C50H63N6O8SSi+ 935.4. Found m/z=935.4 (M+H+).

後処理

  1. stirringThe reaction mixture was stirred over night
  2. additionthen poured
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O (50 mL)
  5. customdried

出典と根拠

ORDレコード
ord-3e5ac4b8714b44548e7e920a2c60aea9
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08394829B2

反応ノート

読み込み中…

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