Ethyl Acetate → HCID 59565321, 화합물

HRID 1962873노트

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HRID 1962873 반응식
[CH3:1]C(C)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-].[C:13]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([O:25][CH:26]([S:36][CH3:37])[C:27]([NH:29][C:30]([CH2:34]O)([CH3:33])[C:31]#[CH:32])=[O:28])=[CH:20][CH:19]=2)#[CH:14].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO.[Cl-].[Na+].O>[C:34]([C:30]([NH:29][C:27](=[O:28])[CH:26]([O:25][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([C:13]#[CH:14])=[CH:24]2)[S:36][CH3:37])([CH3:33])[C:31]#[CH:32])#[CH:1]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 595653502-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamideHCID 86586111Dimethyl-1-diazo-2-oxopropylphosphonate

생성물 1

HCID 59565321HCID 59565321, 화합물

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 57417360Sodium chloride; water용매

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온도
0 °C

실험 절차

A solution of dimethyl-1-diazo-2-oxopropylphosphonate (0.109 g) in dry methanol (2 ml) was added at room temperature to a solution of crude 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-1-methyl-prop-2-ynyl)-2-methylsulfanyl-acetamide (0.125 g) from Stage 5 in methanol (5 ml). The reaction medium was cooled down to 0° C. and potassium carbonate (0.098 g) was added portion wise. The reaction mixture was allowed to warm up to room temperature and stirred for 5.5 hours and then poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with brine and then dried over sodium sulphate. After filtration and concentration under reduced pressure the resulting crude mixture was purified by flash chromatography on silica gel (hexane/ethyl acetate) of N-(1-ethynyl-1-methyl-prop-2-ynyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide as a white solid (m.p.: 148-154° C.).

후처리

  1. temperatureto warm up to room temperature
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted thrice with ethyl acetate
  4. washwashed once with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration and concentration under reduced pressure the resulting crude mixture
  7. customwas purified by flash chromatography on silica gel (hexane/ethyl acetate) of N-(1-ethynyl-1-methyl-prop-2-ynyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide as a white solid (m.p.: 148-154° C.)

출처 및 근거

ORD 기록
ord-a4957ca2add54b339f06a57d8a30ec5e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415272B2

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