Diisopropylethylamine → 4-[(2-{[3-({3-[(4-{2-[4-(Methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)benzyl](pentan-3-yl)amino)ethyl)(methyl)amino]-2,2-dimethyl-4-oxobutanoic acid

HRID 2176010노트

반응식

HRID 2176010 반응식
[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.[CH3:60][C:61]1([CH3:68])[CH2:65][C:64](=[O:66])[O:63][C:62]1=[O:67]>O1CCOCC1>[CH3:41][O:40][C:38]([C:37]1[CH:42]=[CH:43][C:34]([CH2:33][CH2:32][C:29]2[CH:28]=[CH:27][C:26]([NH:25][C:23]([C:22]3[C:21]4[CH2:44][CH2:45][CH2:46][CH2:47][C:20]=4[S:19][C:18]=3[NH:17][C:15]([C:14]3[CH:13]=[C:12]([CH:50]=[CH:49][CH:48]=3)[CH2:11][N:5]([CH:6]([CH2:9][CH3:10])[CH2:7][CH3:8])[CH2:4][CH2:3][N:2]([CH3:1])[C:64](=[O:66])[CH2:65][C:61]([CH3:68])([CH3:60])[C:62]([OH:63])=[O:67])=[O:16])=[O:24])=[CH:31][CH:30]=2)=[CH:35][CH:36]=1)=[O:39]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 870672,2-Dimethylsuccinic anhydrideHCID 90370366HCID 90370366, 화합물

생성물 1

HCID 903701804-[(2-{[3-({3-[(4-{2-[4-(Methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)benzyl](pentan-3-yl)amino)ethyl)(methyl)amino]-2,2-dimethyl-4-oxobutanoic acid수율 84.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
65 °C

실험 절차

To a mixture of 200 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, 48 mg of N-ethyl-N-isopropylpropan-2-amine and 4 mL of dioxane was added 44 mg of 3,3-dimethyldihydrofuran-2,5-dione, followed by stirring overnight at 65° C. The reaction mixture was concentrated under reduced pressure, ethyl acetate and water were added to the residue, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography, thereby obtaining 200 mg of 4-[(2-{[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)benzyl](pentan-3-yl)amino}ethyl)(methyl)amino]-2,2-dimethyl-4-oxobutanoic acid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate and water
  2. additionwere added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bb299870febe41728ca5dc1349edb6b0
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062032B2

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