Sodium Bicarbonate → tert-Butyl (R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl((R)-1-(3-((4-(5-isopropylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)propan-2-yl)carbamate

HRID 1689527ノート

反応式

HRID 1689527 の反応式
[Si:1]([O:8][C@H:9]([C:30]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]2[C:31]=1[CH:32]=[CH:33][C:34](=[O:41])[NH:35]2)[CH2:10][N:11]([C@H:19]([CH3:29])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:42]([C:45]1[S:49][CH:48]=[C:47]([C:50]([N:52]2[CH2:57][C:56]3([CH2:62][CH2:61][NH:60][CH2:59][CH2:58]3)[O:55][CH2:54][CH2:53]2)=[O:51])[CH:46]=1)([CH3:44])[CH3:43].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O.C(O)(=O)C.CN1CCCC1=O>[Si:1]([O:8][C@H:9]([C:30]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]2[C:31]=1[CH:32]=[CH:33][C:34](=[O:41])[NH:35]2)[CH2:10][N:11]([C@H:19]([CH3:29])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:60]2[CH2:59][CH2:58][C:56]3([O:55][CH2:54][CH2:53][N:52]([C:50]([C:47]4[CH:46]=[C:45]([CH:42]([CH3:44])[CH3:43])[S:49][CH:48]=4)=[O:51])[CH2:57]3)[CH2:62][CH2:61]2)[CH:22]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57989215(5-Isopropylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanoneHCID 57989338tert-Butyl (R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

生成物 1

HCID 57989027tert-Butyl (R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl((R)-1-(3-((4-(5-isopropylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)propan-2-yl)carbamate

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

tert-Butyl (R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate (Example 276, step i) (0.476 g) was treated with (5-isopropylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (Example 275, step i) (0.296 g), N-methyl-2-pyrrolidinone (20 mL), acetic acid (0.052 mL) and sodium triacetoxyborohydride (0.294 g), and the mixture was stirred at room temperature overnight. The solution was poured into a mixture of saturated sodium bicarbonate solution and water and extracted three times with diethyl ether. The combined extracts were washed with water and brine, dried (MgSO4) and concentrated in vacuo, then purified by flash chromatography on silica eluted with 1:5:94 NEt3:MeOH:DCM to afford the subtitled compound. Yield 0.471 g.

後処理

  1. extractionextracted three times with diethyl ether
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica
  6. washeluted with 1:5:94 NEt3

出典と根拠

ORDレコード
ord-24c65cd24dcd46aaab21a12942f94078
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

反応ノート

読み込み中…