Pyridine → 2,4-Bis-(N-(Cbz-valinyl)amino)-1,5-diphenyl-3-pentyl 3-(chloromethyl)benzoate

HRID 1078140ノート

反応式

HRID 1078140 の反応式
[C:1]([NH:11][C@H:12]([C:16]([NH:18][CH:19]([CH:27]([OH:54])[CH:28]([NH:36][C:37](=[O:53])[C@H:38]([CH:50]([CH3:52])[CH3:51])[NH:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[Cl:55][CH2:56][C:57]1[CH:58]=[C:59]([CH:63]=[CH:64][CH:65]=1)[C:60](Cl)=[O:61].N1C=CC=CC=1>C(Cl)(Cl)Cl.C(Cl)Cl.CO>[Cl:55][CH2:56][C:57]1[CH:58]=[C:59]([CH:63]=[CH:64][CH:65]=1)[C:60]([O:54][CH:27]([CH:19]([NH:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:28]([NH:36][C:37](=[O:53])[C@H:38]([CH:50]([CH3:52])[CH3:51])[NH:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:61]

参加物

7

反応物 3

HCID 1049PyridineHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 3011026benzyl N-[(1S)-1-[[1-benzyl-3-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-hydroxy-4-phenyl-butyl]carbamoyl]-2-methyl-propyl]carbamate

生成物 1

HCID 228455642,4-Bis-(N-(Cbz-valinyl)amino)-1,5-diphenyl-3-pentyl 3-(chloromethyl)benzoate収率 30%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒4 回

実験手順

The resultant compound of Example 70 (769 mg, 1.04 mmol) was combined with 3-(chloromethyl) benzoyl chloride (395 mg, 2.09 mmol) and pyridine (165 mg, 2.09 mmol) in 10 mL of freshly distilled methylene chloride. The reaction mixture was stirred at ambient temperature under nitrogen for approximately 65 h and then diluted with 150 mL of chloroform. The chloroform solution was washed with 75 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue (1.59 g) was taken up in ~10 mL of methylene chloride and applied to a 1.5×45 cm column of 40 mesh silica gel. The column was eluted @~5 p.s.i. sequentially with 200 mL of methylene chloride, 200 mL of 0.5% methanol in methylene chloride and 200 mL of 1% methanol in methylene chloride to give 275 mg (30% yield) of the title compound; FAB MS M/Z: 889 (M+H)+. The 300 MHz 1H NMR spectrum was consistent with the assigned structure.

後処理

  1. washThe chloroform solution was washed with 75 mL of water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washThe column was eluted @~5 p.s.i

出典と根拠

ORDレコード
ord-6e8fbc78bc7f44ce8a3a7e37c26cab5c
出典データセット
uspto-grants-1996_08
特許番号
US05545750

反応ノート

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