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Diisopropylethylamine → 2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-((4-(cyclopropylmethoxy)benzoyl)amino)pyridin-4-yl)sulfanyl)propanoate

HRID 2277260
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HRID 2277260 반응식
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[C:15]([NH:18][C@@H:19]([CH3:43])[CH2:20][O:21][C:22]1[CH:27]=[C:26]([S:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH:35]([CH2:40][CH3:41])[CH2:36][CH2:37][CH2:38][CH3:39])=[O:32])[C:25]([NH2:42])=[CH:24][N:23]=1)(=[O:17])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>O.CN(C=O)C>[C:15]([NH:18][C@@H:19]([CH3:43])[CH2:20][O:21][C:22]1[CH:27]=[C:26]([S:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH:35]([CH2:40][CH3:41])[CH2:36][CH2:37][CH2:38][CH3:39])=[O:32])[C:25]([NH:42][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)=[CH:14][CH:13]=2)=[CH:24][N:23]=1)(=[O:17])[CH3:16]
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참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 226453014-(Cyclopropylmethoxy)benzoic acidHCID 867313332-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-aminopyridin-4-yl)sulfanyl)propanoate

생성물 1

HCID 86731335
2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-((4-(cyclopropylmethoxy)benzoyl)amino)pyridin-4-yl)sulfanyl)propanoate
수율 52.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

A mixture of 4-(cyclopropylmethoxy)benzoic acid (452 mg), 2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-aminopyridin-4-yl)sulfanyl)propanoate (1.00 g), HATU (0.893 g), N,N-diisopropylethylamine (0.821 mL) and DMF (10 mL) was stirred at 70° C. for 5 days. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.740 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-c97186785b6d4da38de27f7b4fb28cd5
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133129B2

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