Diethylamine → 5-(1-Diethylcarbamoyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966501노트

반응식

HRID 966501 반응식
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][C:21]([C:24]([OH:26])=O)([CH3:23])[CH3:22])[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCCCCC.C(OCC)(=O)C>C(OC(=O)C)C>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][C:21]([C:24](=[O:26])[N:30]([CH2:31][CH3:32])[CH2:28][CH3:29])([CH3:22])[CH3:23])[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8021DiethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21226206Ethyl acetate hexaneHCID 233938135-(1-Carboxy-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

생성물 1

HCID 101592625-(1-Diethylcarbamoyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester수율 12%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

5-(1-Carboxy-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (1.0 g, 2.76 mmol, 1.0 eq) was dissolved in ethylacetate (100 mL), and treated with diethylamine (0.241 g, 3.3 mmol, 1.2 eq) followed by HBTU (0.446 g, 3.3 mmol, 1.2 eq). The reaction mixture was stirred at room temperature for 24 hours and was followed by TLC (hexane/ethyl acetate 1/1). The reaction was quenched with aqueous sodium bicarbonate, extracted with ethyl acetate, and the organic layers dried over sodium sulfate, evaporated, and loaded on silica gel, followed by flash chromatography (hexane/ethyl acetate 1/1). 0.109 g of the product was obtained, 12% yield. LC/MS (ESI+) 422.52 (M+1) (C25H30N2O4).

후처리

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layers dried over sodium sulfate
  4. customevaporated

출처 및 근거

ORD 기록
ord-aec778a9fa7045b5b5bd9e8ea0a68821
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951848B2

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