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Potassium tert-butoxide → tert-butyl ((2R,6S,7R,13aS,14aR,16aS,Z)-2-((3-(dimethylamino)-6-methoxyisoquinolin-1-yl)oxy)-7,9-dimethyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate

HRID 1852127
ノート
印刷プレビュー

反応式

HRID 1852127 の反応式
[OH:1][C@H:2]1[CH2:42][N:5]2[C:6](=[O:41])[C@@H:7]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C@H:8]([CH3:32])[CH2:9][CH:10]([CH3:31])[CH2:11][CH2:12][CH:13]=[CH:14][C@@H:15]3[CH2:20][C@@:16]3([C:21](=[O:30])[NH:22][S:23]([C:26]3([CH3:29])[CH2:28][CH2:27]3)(=[O:25])=[O:24])[NH:17][C:18](=[O:19])[C@@H:4]2[CH2:3]1.Cl[C:44]1[C:53]2[C:48](=[CH:49][C:50]([O:54][CH3:55])=[CH:51][CH:52]=2)[CH:47]=[C:46]([N:56]([CH3:58])[CH3:57])[N:45]=1.CC(C)([O-])C.[K+]>CS(C)=O>[CH3:57][N:56]([CH3:58])[C:46]1[N:45]=[C:44]([O:1][C@H:2]2[CH2:42][N:5]3[C:6](=[O:41])[C@@H:7]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C@H:8]([CH3:32])[CH2:9][CH:10]([CH3:31])[CH2:11][CH2:12][CH:13]=[CH:14][C@@H:15]4[CH2:20][C@@:16]4([C:21](=[O:30])[NH:22][S:23]([C:26]4([CH3:29])[CH2:28][CH2:27]4)(=[O:24])=[O:25])[NH:17][C:18](=[O:19])[C@@H:4]3[CH2:3]2)[C:53]2[C:48]([CH:47]=1)=[CH:49][C:50]([O:54][CH3:55])=[CH:51][CH:52]=2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 23665647Potassium tert-butoxideHCID 594234521-chloro-6-methoxy-N,N-dimethylisoquinolin-3-amineHCID 71004914tert-butyl ((2R,6S,7R,13aS,14aR,16aS,Z)-2-hydroxy-7,9-dimethyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate

生成物 1

HCID 86683201
tert-butyl ((2R,6S,7R,13aS,14aR,16aS,Z)-2-((3-(dimethylamino)-6-methoxyisoquinolin-1-yl)oxy)-7,9-dimethyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a mixture of tert-butyl ((2R,6S,7R,13aS,14aR,16aS,Z)-2-hydroxy-7,9-dimethyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate (150 mg, 0.246 mmol),1-chloro-6-methoxy-N,N-dimethylisoquinolin-3-amine (69.8 mg, 0.295 mmol), and potassium tert-butoxide (138 mg, 1.228 mmol) was added DMSO (5 mL) and then the mixture was sonicated for 15 min. The resulting solution was stirred for 4 h at room temperature. The reaction was quenched with water, acidified with 6 N HCl to pH=4, and extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, filtered, and concentrated to give the crude tert-butyl ((2R,6S,7R,13aS,14aR,16aS,Z)-2-((3-(dimethylamino)-6-methoxyisoquinolin-1-yl)oxy)-7,9-dimethyl-14a-(((1-methylcyclopropyl)sulfonyl)carbamoyl)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate that was used in the next step as is. MS: MS m/z 811.6 (M++1).

後処理

  1. customthe mixture was sonicated for 15 min
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic layer was collected
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-1589d6fbbd4346e9aee70d6081347939
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08957203B2

反応ノート

読み込み中…

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