Triethylamine → (R)-tert-Butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(4-(2-(4-(2-phenylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl)carbamate

HRID 1689493

反応式

HRID 1689493 の反応式
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:17][C@H:18]([OH:30])[C:19]2[C:27]3[S:26][C:25](=[O:28])[NH:24][C:23]=3[C:22]([OH:29])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1)(=O)=O.[C:38]1([C:44]2[S:45][CH:46]=[C:47]([C:49]([N:51]3[CH2:56][C:55]4([CH2:61][CH2:60][NH:59][CH2:58][CH2:57]4)[O:54][CH2:53][CH2:52]3)=[O:50])[N:48]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C>CC#N>[OH:30][C@H:18]([C:19]1[C:27]2[S:26][C:25](=[O:28])[NH:24][C:23]=2[C:22]([OH:29])=[CH:21][CH:20]=1)[CH2:17][N:16]([CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:59]2[CH2:60][CH2:61][C:55]3([O:54][CH2:53][CH2:52][N:51]([C:49]([C:47]4[N:48]=[C:44]([C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=5)[S:45][CH:46]=4)=[O:50])[CH2:56]3)[CH2:57][CH2:58]2)=[CH:10][CH:11]=1)[C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:37])[CH3:36]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 57989130(2-Phenylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanoneHCID 57989363(R)-2-(4-((tert-butoxycarbonyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)amino)methyl)phenoxy)ethyl methanesulfonate

生成物 1

HCID 57989175(R)-tert-Butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(4-(2-(4-(2-phenylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzyl)carbamate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of (R)-2-(4-((tert-butoxycarbonyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)amino)methyl)phenoxy)ethyl methanesulfonate (example 108, step c) (0.619 g) in MeCN (3 mL) was added dropwise to a solution of (2-phenylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 112, step b) (0.274 g) and triethylamine (0.22 mL) in MeCN (7.3 mL) at RT under argon. The resulting mixture was stirred at 80° C. under argon for 16 h. After cooling to RT the solvent was removed in vacuo. The residue was taken up in DCM, washed with brine and water, dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with 0-70% EtOAc in petroleum ether (40-60° C.) to give the subtitled compound as a yellow solid. Yield 0.42 g.

後処理

  1. temperatureAfter cooling to RT the solvent
  2. customwas removed in vacuo
  3. washwashed with brine and water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 0-70% EtOAc in petroleum ether (40-60° C.)

出典と根拠

ORDレコード
ord-0ba0052ff4804209892c82fe208d426e
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

関連ノート

読み込み中…