Diisopropylethylamine → methyl 4-{2-[4-({[2-({3-[(4S)-4,7-dimethyl-3,6-dioxo-10-(pentan-3-yl)-2-oxa-5,7,10-triazaundecan-11-yl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl)amino)phenyl]ethyl}benzoate

HRID 2175996ノート

反応式

HRID 2175996 の反応式
[CH3:1][NH:2][CH2:3][CH2:4][N:5]([CH2:11][C:12]1[CH:13]=[C:14]([CH:48]=[CH:49][CH:50]=1)[C:15]([NH:17][C:18]1[S:19][C:20]2[CH2:47][CH2:46][CH2:45][CH2:44][C:21]=2[C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)=[CH:28][CH:27]=1)=[O:24])=[O:16])[CH:6]([CH2:9][CH3:10])[CH2:7][CH3:8].C(N(C(C)C)C(C)C)C.[N:60]([C@@H:63]([CH3:68])[C:64]([O:66][CH3:67])=[O:65])=[C:61]=[O:62].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C1COCC1>[CH3:68][C@H:63]([NH:60][C:61](=[O:62])[N:2]([CH3:1])[CH2:3][CH2:4][N:5]([CH:6]([CH2:9][CH3:10])[CH2:7][CH3:8])[CH2:11][C:12]1[CH:13]=[C:14]([CH:48]=[CH:49][CH:50]=1)[C:15]([NH:17][C:18]1[S:19][C:20]2[CH2:47][CH2:46][CH2:45][CH2:44][C:21]=2[C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:42][CH:43]=2)=[CH:28][CH:27]=1)=[O:24])=[O:16])[C:64](=[O:65])[O:66][CH3:67]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 7019162methyl (2S)-2-isocyanatopropanoateHCID 90370366HCID 90370366、化合物

生成物 1

HCID 90370402methyl 4-{2-[4-({[2-({3-[(4S)-4,7-dimethyl-3,6-dioxo-10-(pentan-3-yl)-2-oxa-5,7,10-triazaundecan-11-yl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl)amino)phenyl]ethyl}benzoate収率 97.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 250 mg of methyl 4-[2-(4-{[(2-{[3-({[2-(methylamino)ethyl](pentan-3-yl)amino}methyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate, 0.20 mL of N-ethyl-N-isopropylpropan-2-amine and 10 mL of THF under ice cooling was added 70 mg of methyl(S)-(−)-2-isocyanatopropionate, followed by stirring for 1 hour at the same temperature and then for 2 hours at room temperature. Ethyl acetate and an aqueous sodium hydrogen carbonate solution were added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (10% methanol/chloroform), thereby obtaining 290 mg methyl 4-{2-[4-({[2-({3-[(4S)-4,7-dimethyl-3,6-dioxo-10-(pentan-3-yl)-2-oxa-5,7,10-triazaundecan-11-yl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate.

後処理

  1. waitfor 2 hours at room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (10% methanol/chloroform)

出典と根拠

ORDレコード
ord-c6e17f72b0974e5694faa8e814561632
出典データセット
uspto-grants-2015_06
特許番号
US09062032B2

反応ノート

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