Triethylamine → benzyl (3R)-3-[(biphenyl-4-carbonyl)amino]-4-(3-cyanophenoxy)butyrate

HRID 747702ノート

反応式

HRID 747702 の反応式
Cl.[NH2:2][C@@H:3]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=1)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C(N(CC)CC)C.[C:32]1([C:38]2[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O.O>[C:38]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:39]=[CH:40][C:41]([C:42]([NH:2][C@@H:3]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=2)[CH2:4][C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6])=[O:43])=[CH:45][CH:46]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 86760704benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride

生成物 1

HCID 86760703benzyl (3R)-3-[(biphenyl-4-carbonyl)amino]-4-(3-cyanophenoxy)butyrate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

310 mg (1.0 mmol) of benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride was dissolved in 10 ml of dimethylformamide. 0.18 ml (1.3 mmol) of triethylamine was added to the solution. 282 mg (1.3 mmol) of 4-phenylbenzoyl chloride was added to the resultant mixture under cooling with ice, and they were stirred for 30 minutes. The temperature was elevated to room temperature, and the reaction mixture was stirred for additional 2 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

後処理

  1. temperatureunder cooling with ice, and they
  2. customwas elevated to room temperature
  3. stirringthe reaction mixture was stirred for additional 2 hours
  4. customThe reaction liquid
  5. extractionAfter the extraction with ethyl acetate
  6. washthe organic layer was successively washed with water, 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by the silica gel column chromatography

出典と根拠

ORDレコード
ord-906c86771629420f8b5e9fcf54407058
出典データセット
uspto-grants-2008_07
特許番号
US07396844B1

反応ノート

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