Triethylamine → tert-butyl 3-[2-ethyl-4-[(Z)-N'-hydroxycarbamimidoyl]-6-methylphenyl]propanoate

HRID 2040806ノート

反応式

HRID 2040806 の反応式
[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][C:10]=1[CH2:18][CH3:19])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:22][OH:23].CCN(CC)CC>CO>[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16](=[NH:17])[NH:22][OH:23])=[CH:11][C:10]=1[CH2:18][CH3:19])([CH3:3])([CH3:4])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 685503513-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid tert-butyl ester

生成物 1

HCID 178436624tert-butyl 3-[2-ethyl-4-[(Z)-N'-hydroxycarbamimidoyl]-6-methylphenyl]propanoate収率 98.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid tert-butyl ester (37.0 g, 135 mmol), hydroxylamine hydrochloride (14.1 g, 203 mmol) and NEt3 (27.4 g, 271 mmol) in MeOH (400 mL) is heated to reflux for 7 h before it is cooled to rt. The solvent is evaporated and the residue is taken up in isopropylacetate (500 mL) and washed twice with water (500 mL). The org. extract is dried over MgSO4, filtered, evaporated and dried to give 3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenyl]-propionic acid tert-butyl ester (40.8 g) as a pale yellow solid; 1H NMR δ 1.26 (t, J=7.5 Hz, 3 H), 1.49 (s, 9 H), 2.33-2.41 (m, 5 H), 2.66-2.74 (m, 2 H), 2.93-3.01 (m, 2 H), 4.85 (s, 1 H), 7.28 (s, 2 H).

後処理

  1. temperatureto reflux for 7 h before it
  2. customThe solvent is evaporated
  3. washwashed twice with water (500 mL)
  4. extractionextract
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried

出典と根拠

ORDレコード
ord-02c73c91283a49d08cff96752d7d89f4
出典データセット
uspto-grants-2013_11
特許番号
US08580824B2

反応ノート

読み込み中…