Acetic Acid → Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(3-{2-[(R)-2-(tert-Butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]-ethyl}phenylcarbamoyl)propyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

HRID 1055303ノート

反応式

HRID 1055303 の反応式
C([N:8]([CH2:51][C@@H:52]([C:61]1[CH:70]=[CH:69][C:68]([O:71]CC2C=CC=CC=2)=[C:67]2[C:62]=1[CH:63]=[CH:64][C:65](=[O:79])[NH:66]2)[O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:56])[CH3:55])[CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]([CH2:20][CH2:21][CH2:22][N:23]([CH3:50])[C:24]([CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([O:34][C:35](=[O:49])[NH:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:30][CH2:29]2)=[O:25])=[O:19])[CH:14]=[CH:15][CH:16]=1)C1C=CC=CC=1.C(O)(=O)C.O>CO.[OH-].[Pd+2].[OH-]>[Si:54]([O:53][C@H:52]([C:61]1[CH:70]=[CH:69][C:68]([OH:71])=[C:67]2[C:62]=1[CH:63]=[CH:64][C:65](=[O:79])[NH:66]2)[CH2:51][NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]([CH2:20][CH2:21][CH2:22][N:23]([CH3:50])[C:24]([CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([O:34][C:35](=[O:49])[NH:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH2:30][CH2:29]2)=[O:25])=[O:19])[CH:14]=[CH:15][CH:16]=1)([C:57]([CH3:60])([CH3:58])[CH3:59])([CH3:55])[CH3:56]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 86704960Biphenyl-2-ylcarbamic Acid 1-[2-({3-[3-(2-{Benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethyl]-amino}ethyl)phenylcarbamoyl]propyl}methylcarbamoyl)ethyl]piperidin-4-yl Ester

生成物 1

HCID 86704961Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(3-{2-[(R)-2-(tert-Butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]-ethyl}phenylcarbamoyl)propyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

To a stirred solution of biphenyl-2-ylcarbamic acid 1-[2-({3-[3-(2-{benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2- (tert-butyldimethylsilanyloxy)ethyl]-amino}ethyl)phenylcarbamoyl]propyl}methylcarbamoyl)ethyl]piperidin-4-yl ester (258 mg, 0.238 mmol) in MeOH (3 mL) at room temperature was added a solution of acetic acid in water (17.4 M, 41.4 μL, 0.720 mmol). The resulting solution was purged with nitrogen (3 cycles of vacuum following by dry nitrogen) and then palladium hydroxide (47 mg, 0.34 mmol) was added. This mixture was again purged with nitrogen and then with hydrogen (5×) and then stirred at room temperature under hydrogen (balloon with submerged needle) for 6 h. LC-MS (Method 2-90) showed product was present (Rt 3.71 min; m/z 903.6 [M+H]+). The reaction mixture was filtered through a membrane filter and the filtrate was concentrated under reduced pressure to give the title compound, which was used in the next reaction without further purification.

後処理

  1. customThe resulting solution was purged with nitrogen (3 cycles of vacuum following by dry nitrogen)
  2. customThis mixture was again purged with nitrogen
  3. filtrationThe reaction mixture was filtered through a membrane
  4. filtrationfilter
  5. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-924b8d82f89749c8a1f6d8958bfd1183
出典データセット
uspto-grants-2016_07
特許番号
US09394275B2

反応ノート

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