1-Hydroxybenzotriazole → 3-Mercaptopyridine-2-carboxylic acid N-((methoxycarbonyl)methyl)amide

HRID 53831

反応式

HRID 53831 の反応式
[SH:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.ON1C2C=CC=CC=2N=N1.COS(C1C=CC(C)=CC=1)(=O)=O.C1(N=C=NCCN2CCOCC2)CCCCC1.Cl.[CH3:51][O:52][C:53](=[O:56])[CH2:54][NH2:55]>CN(C=O)C.C(N1CCOCC1)C.C(OCC)(=O)C.CCCCCCC>[CH3:51][O:52][C:53]([CH2:54][NH:55][C:8]([C:3]1[C:2]([SH:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])=[O:56]

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 1190703-Mercaptopicolinic acidHCID 122755Glycine methyl ester hydrochlorideHCID 9954069N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate

生成物 1

HCID 153381943-Mercaptopyridine-2-carboxylic acid N-((methoxycarbonyl)methyl)amide

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 7525Ethylmorpholine溶媒HCID 21899848Ethylacetate heptane溶媒

実験手順

1.69 g of 3-mercaptopyridine-2-carboxylic acid were dissolved in 20 ml of DMF and 7.5 ml of N-ethylmorpholine, 1.7 g of 1-hydroxy-1H-benzotriazole, 5 g of N-cyclohexyl-N'-(2-morpholinoethyl)-carbodiimide methyl-p-toluenesulfonate and 4.3 g of glycine methyl ester hydrochloride were added successively at room temperature and whilst stirring. After having been stirred for 12 hours, the mixture was partitioned between a saturated aqueous solution of ammonium chloride and dichloromethane and the organic phase was dried and concentrated by evaporation; the residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptane); yield, 0.65 g of colourless crystals of m.p. 178°-179° C. (ethyl acetate/heptane).

後処理

  1. stirringAfter having been stirred for 12 hours
  2. customthe mixture was partitioned between a saturated aqueous solution of ammonium chloride and dichloromethane
  3. customthe organic phase was dried
  4. concentrationconcentrated by evaporation
  5. customthe residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptane)
  6. customyield

出典と根拠

ORDレコード
ord-878e2a359c054f568ea7025c36f50a11
出典データセット
uspto-grants-1997_04
特許番号
US05620995

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