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Triethylamine → HCID 68700016, 화합물

HRID 1990893
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HRID 1990893 반응식
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][C:11](Cl)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][C:11]([NH:28][CH:25]3[CH2:24][CH2:23][N:22]([C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH2:27][CH2:26]3)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 68406054Methyl 2-chloro-1,3-benzoxazole-7-carboxylate

생성물 1

HCID 68700016HCID 68700016, 화합물수율 85.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-chloro-benzooxazole-7-carboxylic acid methyl ester (1.50 g, 7.08 mmol, 1.0 equiv; example 252/step 3) in acetonitrile (23 mL) was added 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.42 g, 7.08 mmol, 1.0 equiv) and triethylamine (0.79 g, 7.79 mmol, 1.1 equiv). After stirring for 48 h at rt, the reaction mixture was poured on ice, the solution extracted with ethyl acetate (2×100 mL) and the combined organic phases washed with water (2×100 mL) and a conc. solution of sodium chloride (100 mL). The organic phase was dried over MgSO4, concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with hexane/ethyl acetate (1:1) providing 2.27 g (85%) of the title compound. MS (ISP): 376.4 [M+H]+.

후처리

  1. additionthe reaction mixture was poured on ice
  2. extractionthe solution extracted with ethyl acetate (2×100 mL)
  3. washthe combined organic phases washed with water (2×100 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe crude reaction product
  7. custompurified with column chromatography on silica eluting with hexane/ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-06a707bf78944f95a69708eddd1ac5b0
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07645753B2

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