Ammonia → Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate

HRID 2037352ノート

反応式

HRID 2037352 の反応式
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1[C:18]([CH3:19])=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:27]C=2C=1.CCN=C=NCCCN(C)C.Cl.N>C(O)(C)C>[C:1]([O:5][C:6](=[O:7])[CH2:8][CH2:9][C:10]1[C:18]([CH3:19])=[CH:17][C:13]([C:14](=[O:15])[NH2:27])=[CH:12][C:11]=1[CH3:20])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 594979324-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid

生成物 1

HCID 11849882Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate収率 94.2%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒2 回

実験手順

To a suspension of 4-(2-tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid (8.00 g, 28.7 mmol) in isopropanol (100 mL), HOBt (4.27 g, 31.6 mmol) followed by EDC hydrochloride (6.34 g, 33.1 mmol) is added. After stirring at rt for 1 h, 25% aq. ammonia (16.1 mL) is added. Stirring is continued for 30 min before the isopropanol is evaporated under reduced pressure. The remaining solution is diluted with isopropyl acetate (200 mL), washed three times with approximately 0.5 N aq. NaHCO3 solution (100 mL) followed by water (50 mL), dried over MgSO4, filtered, concentrated and dried to give 3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (7.5 g) as an off-white solid.

後処理

  1. additionis added
  2. stirringStirring
  3. customis evaporated under reduced pressure
  4. additionThe remaining solution is diluted with isopropyl acetate (200 mL)
  5. washwashed three times with approximately 0.5 N aq. NaHCO3 solution (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried

出典と根拠

ORDレコード
ord-e433909f4eef40978179ba6401164e03
出典データセット
uspto-grants-2013_11
特許番号
US08575200B2

反応ノート

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