Potassium Carbonate → N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3(R)-(3-picolyloxy)butanamide

HRID 2209722ノート

反応式

HRID 2209722 の反応式
[C:1]([O:5][NH:6][C:7](=[O:24])[C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C@H:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].Cl.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Cl)[CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]([O:5][NH:6][C:7](=[O:24])[C@H:8]([N:12]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:32][C:28]1[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=1)[C@H:9]([O:11][CH2:32][C:28]1[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=1)[CH3:10])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochloride2 回HCID 22856309N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl]-amino]-3(R)-hydroxybutanamide

生成物 1

HCID 86749033N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3(R)-(3-picolyloxy)butanamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl]amino]-3(R)-hydroxybutanamide (3.04 g, 8.44 mmol) in dimethylformamide (150 mL) is added 3-picolyl chloride hydrochloride (1.45 g, 8.87 mmol) followed by potassium carbonate (11.65 g, 84.4 mmol). The reaction mixture is stirred at room temperature overnight, then heated to 45° C. for 5 hours. An additional amount of 3-picolyl chloride hydrochloride (692.0 mg, 4.23 mmol) is added at this point. The reaction mixture is stirred at 45° C. for 10 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The crude product is purified by silica gel chromatography (ethyl acetate, then 5% methanol/methylene chloride) to give N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3(R)-(3-picolyloxy)butanamide.

後処理

  1. temperatureheated to 45° C. for 5 hours
  2. stirringThe reaction mixture is stirred at 45° C. for 10 hours
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by silica gel chromatography (ethyl acetate

出典と根拠

ORDレコード
ord-74c43f554adf4ac2872e3f13ca8eea9e
出典データセット
uspto-grants-1995_10
特許番号
US05455258

反応ノート

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