1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59548531, 화합물

HRID 1879670

반응식

HRID 1879670 반응식
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[CH2:26]([O:28][CH:29]([O:32][CH2:33][CH3:34])[CH2:30][NH2:31])[CH3:27].CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1>C1COCC1.O>[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:5]=1[C:6]([NH:31][CH2:30][CH:29]([O:32][CH2:33][CH3:34])[O:28][CH2:26][CH3:27])=[O:8])([O-:3])=[O:2]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 695242,2-DiethoxyethylamineHCID 81531DiisopropylethylamineHCID 2573264-Tert-butyl-2-nitrobenzoic acidHCID 178526939HCID 178526939, 화합물

생성물 1

HCID 59548531HCID 59548531, 화합물수율 40.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

2-nitro-4-tert-butylbenzoic acid (1.5 g, 7 mmol, prepared according to J. Am. Chem. Soc, 1955, 77, 5441) was stirred in THF at room temperature, 1.7 mL diisopropylethyl amine (13 mmol, 2 eq) was added, followed by 984 mg (7.7 mmol, 1.1 eq) 2-amino acetaldehyde diethylacetal. (3-Dimethylamino-propyl)-ethyl-carbodiimide (1.55 g, 8 mmol, 1.2 eq) was added, followed by a catalytic amount (ca. 50 mgs) hydroxybenzotriazole hydrate. The mixture was stirred at room temperature for 16 hours, diluted with water, extracted with diethyl ether 3×, the ether layers were washed with water, brine, and dried over MgSO4. Removal of solvent under vacuum, followed by chromatography on silica gel, eluting with 25% ethyl acetate in hexanes, gave the title compound 0.950 g, (M+H)+=224.

후처리

  1. extractionextracted with diethyl ether 3×
  2. washthe ether layers were washed with water, brine
  3. dry with materialdried over MgSO4
  4. customRemoval of solvent under vacuum
  5. washeluting with 25% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-3ffc9684a3b04f1aae46226650e0c184
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318719B2

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