Triethylamine → HCID 57539227、化合物

HRID 601962ノート

反応式

HRID 601962 の反応式
[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:9]([CH2:13][O:14][CH:15]([F:17])[F:16])[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[F:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH2:46])=[CH:43][CH:42]=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:9]([CH2:13][O:14][CH:15]([F:16])[F:17])[C:10]([NH:46][CH2:45][C:44]1[CH:47]=[CH:48][C:41]([F:40])=[CH:42][CH:43]=1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 673264-FluorobenzylamineHCID 57539219HCID 57539219、化合物

生成物 1

HCID 57539227HCID 57539227、化合物収率 89.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-(dibenzylamino)-3-(difluoromethoxy)propanoic acid (335.4 mg, 1 mmol) and triethylamine (404.8 mg, 4 mmol) in THF (5 mL) at −5° C., isobutyl chloroformate (143.5 mg, 1.05 mmol) was added dropwise. After 20 minutes, 4-fluorobenzylamine (137.5 mg, 1.1 mmol) was added and the reaction mixture allowed to warm up to room temperature. The mixture then was diluted with ethyl acetate and washed with water, 0.5 N HCl and Brine. The organic layer was dried over magnesium sulphate, concentrated with silica gel and purified by column chromatography, eluting with 10˜20% ethyl acetate in hexanes, to give 2-dibenzylamino-3-difluoromethoxy-N-(4-fluorobenzyl)propionamide (395 mg, 89.2%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.56 (t, 1H), 6.98-7.32 (m, 14H), 6.35 (wt, 1H), 4.61 (dd, 1H), 4.41 (m, 3H), 3.86 (d, 2H), 3.70 (d, 2H) and 3.68 (m, 1H).

後処理

  1. washwashed with water, 0.5 N HCl and Brine
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. concentrationconcentrated with silica gel
  4. custompurified by column chromatography
  5. washeluting with 10˜20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-ef216c0586494acfa8c75469e41cfd2b
出典データセット
uspto-grants-2011_03
特許番号
US07902401B2

反応ノート

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