Ethyl Acetate → HCID 59565321、化合物

HRID 1962873ノート

反応式

HRID 1962873 の反応式
[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]

参加物

7

反応物 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

生成物 1

HCID 59565321HCID 59565321、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

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.).

後処理

  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.)

出典と根拠

ORDレコード
ord-a4957ca2add54b339f06a57d8a30ec5e
出典データセット
uspto-grants-2013_04
特許番号
US08415272B2

反応ノート

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