Triethylamine → (2R)-N-[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]-6-nitro-3,4-dihydro-2H-chromene-2-carboxamide

HRID 432098ノート

反応式

HRID 432098 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C@@H:9]([C:14]([OH:16])=O)[CH2:8][CH2:7]2)([O-:3])=[O:2].[NH2:17][CH2:18][C@@H:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[OH:20].C(N(CC)CC)C.OC1C2N=NNC=2C=CC=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[OH:20][C@H:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:18][NH:17][C:14]([C@H:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[O:10]1)=[O:16]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 23556080(R)-2-amino-1-(pyridin-3-yl)ethanolHCID 69139201(2R)-6-Nitro-3,4-dihydro-2H-chromene-2-carboxylic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 59118200(2R)-N-[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]-6-nitro-3,4-dihydro-2H-chromene-2-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(2R)-6-Nitro-3,4-dihydro-2H-chromene-2-carboxylic acid (4.1 g, 18 mmol) and (1R)-2-amino-1-(3-pyridinyl)ethanol (5.0 g, 24 mmol) (both described in U.S. Pat. No. 6,051,586) were suspended in CH2Cl2 and stirred vigorously. Triethylamine (9.2 mL, 66 mmol) was added followed by hydroxybenzotriazole (4.9 g, 36 mmol) and EDCI (6.9 g, 36 mmol), and the reaction was stirred overnight. After 18 hours, TLC showed no remaining acid starting material, so the reaction was partitioned between water and CH2Cl2 and the organic layer was washed 3×100 mL of water. The organic layer was washed with 1N HCl, which removed the product into the aqueous layer. This aqueous layer was washed with CH2Cl2 and the organic was discarded. The aqueous solution was then basified and became cloudy with a white precipitate. The basified mixture was extracted with 3×100 mL of CH2Cl2.

後処理

  1. stirringthe reaction was stirred overnight
  2. customso the reaction was partitioned between water and CH2Cl2
  3. washthe organic layer was washed 3×100 mL of water
  4. washThe organic layer was washed with 1N HCl, which
  5. customremoved the product into the aqueous layer
  6. washThis aqueous layer was washed with CH2Cl2
  7. extractionThe basified mixture was extracted with 3×100 mL of CH2Cl2

出典と根拠

ORDレコード
ord-5cce06ae5a6842d29bd5a98c53e65c47
出典データセット
uspto-grants-2003_12
特許番号
US06660752B2

反応ノート

読み込み中…