Triethylamine → [1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]carbamic acid tert-butyl ester

HRID 1443631ノート

反応式

HRID 1443631 の反応式
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:12](=[O:29])[NH:13][C:14]1[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=1[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[CH2:31](N(CC)CC)C.C(N[C@@H](C(O)=O)C(C)C)(OC(C)(C)C)=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:12](=[O:29])[NH:13][C:14]1[CH:19]=[C:18]([CH3:31])[CH:17]=[CH:16][C:15]=1[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68558928[1-(2-Benzylamino-5-bromo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

生成物 1

HCID 66886932[1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of [1-(2-benzylamino-5-bromo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester (250 mg, 0.9 mmol) and triethylamine (0.19 ml, 1.35 mmol) in dry DMF (5 ml), was added Boc-D-valine (290 mg, 1.35 mmol) followed by TBTU (290 mg, 0.9 mmol,). The reaction mixture was stirred at room temperature overnight. Ethyl acetate was added. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered, and the filtrated was concentrated in vacuo. The crude material was purified by flash chromatography to yield [1-(2-Benzylamino-5-methyl-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester.

後処理

  1. washThe organic layer was washed with saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrated was concentrated in vacuo
  5. customThe crude material was purified by flash chromatography

出典と根拠

ORDレコード
ord-a3720bfb3d094bc0bbe0aeacbd661c38
出典データセット
uspto-grants-2010_02
特許番号
US07662581B1

反応ノート

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