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

HRID 2176042ノート

反応式

HRID 2176042 の反応式
[N+](C1C=CC([O:8][C:9]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=O)=CC=1)([O-])=O.[CH3:19][NH:20][CH2:21][CH2:22][N:23]([CH2:29][C:30]1[CH:31]=[C:32]([CH:66]=[CH:67][CH:68]=1)[C:33]([NH:35][C:36]1[S:37][C:38]2[CH2:65][CH2:64][CH2:63][CH2:62][C:39]=2[C:40]=1[C:41]([NH:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][CH2:51][C:52]2[CH:61]=[CH:60][C:55]([C:56]([O:58][CH3:59])=[O:57])=[CH:54][CH:53]=2)=[CH:46][CH:45]=1)=[O:42])=[O:34])[CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26].C(N(C(C)C)C(C)C)C>C1COCC1>[CH3:19][N:20]([CH2:21][CH2:22][N:23]([CH:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[CH2:29][C:30]1[CH:31]=[C:32]([CH:66]=[CH:67][CH:68]=1)[C:33]([NH:35][C:36]1[S:37][C:38]2[CH2:65][CH2:64][CH2:63][CH2:62][C:39]=2[C:40]=1[C:41]([NH:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][CH2:51][C:52]2[CH:53]=[CH:54][C:55]([C:56]([O:58][CH3:59])=[O:57])=[CH:60][CH:61]=2)=[CH:46][CH:45]=1)=[O:42])=[O:34])[C:9](=[O:8])[O:11][CH2:12][C:13](=[O:14])[O:15][CH3:16]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 90370366HCID 90370366、化合物HCID 90377585Methyl {[(4-nitrophenoxy)carbonyl]oxy}acetate

生成物 1

HCID 90370367Methyl 4-{2-[4-({[2-({3-[7-methyl-3,6-dioxo-10-(pentan-3-yl)-2,5-dioxa-7,10-diazaundecan-11-yl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate収率 97.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 100 mg of methyl {[(4-nitrophenoxy)carbonyl]oxy}acetate and 5.0 mL of THF was added to a mixture of 180 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, 0.15 mL of N-ethyl-N-isopropylpropan-2-amine, and 5.0 mL of THF under ice cooling, followed by stirring for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added to the residue, followed by extraction with ethyl acetate. The organic layer was washed sequentially with a saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane:chloroform=4:6), thereby obtaining 204 mg of methyl 4-{2-[4-({[2-({3-[7-methyl-3,6-dioxo-10-(pentan-3-yl)-2,5-dioxa-7,10-diazaundecan-11-yl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additiona saturated aqueous sodium hydrogen carbonate solution were added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed sequentially with a saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane:chloroform=4:6)

出典と根拠

ORDレコード
ord-cbaa58b55a1b48c8a4947b199f586ea6
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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