1-Hydroxybenzotriazole → Ethyl 2-(2-(2-imino-4-oxothiazolidin-5-yl)acetamido)-4,5-dimethylthiophene-3-carboxylate

HRID 229451

反応式

HRID 229451 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[NH:13][C:14](=[O:20])[CH:15]=[CH:16][C:17](O)=[O:18])=[O:5])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:43][C:44]([NH2:46])=[S:45]>CN(C)C=O.C(OCC)(=O)C>[NH2:46][C:44]1[S:45][CH:16]([CH2:15][C:14]([NH:13][C:7]2[S:8][C:9]([CH3:12])=[C:10]([CH3:11])[C:6]=2[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:20])[C:17](=[O:18])[N:43]=1

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 6815482-(3-Carboxy-acryloylamino)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl esterHCID 2723790ThioureaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 2878630Ethyl 2-(2-(2-imino-4-oxothiazolidin-5-yl)acetamido)-4,5-dimethylthiophene-3-carboxylate収率 51%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 2-(3-Carboxy-acryloylamino)-4,5-dimethyl-thiophene-3-carboxylic acid ethyl ester (2.97 g, 10.0 mmol) in 50 mL of N,N-dimethyl-formamide was added N-hydroxy-benzotriazole (1.48 g, 11.0 mmol) and 1-[3-(dimethylamino) propyl]-3-ethyl-carbodiimide hydrochloride (2.88 g, 15.0 mmol). The reaction mixture was stirred at room temperature for 10 minutes and thiourea (0.84 g, 11.0 mmol) was added. The reaction mixture was stirred at room temperature for another 30 minutes and was heated at 60° C. for 12 hours. The reaction mixture was diluted with 250 mL of ethyl acetate and was washed with 100 mL of water and 100 mL of brine. The organic layer was collected, dried over sodium sulfate and concentrated. The residue was load on a 120 g silica gel column and purified by flash chromatography (eluted with a gradient of 0 to 10% ethyl acetate/hexanes). Ethyl 2-{[(2-amino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl) acetyl]amino}-4,5-dimethylthiophene-3-carboxylate (1.80 g, 51% yield) was produced.

後処理

  1. stirringThe reaction mixture was stirred at room temperature for another 30 minutes
  2. temperaturewas heated at 60° C. for 12 hours
  3. washwas washed with 100 mL of water and 100 mL of brine
  4. customThe organic layer was collected
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by flash chromatography (
  8. washeluted with a gradient of 0 to 10% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-1942ab2eb6dd4fdf969d7c05f33a23f1
出典データセット
uspto-grants-2009_07
特許番号
US07563813B2

関連ノート

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