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

HRID 229451

반응식

HRID 229451 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1942ab2eb6dd4fdf969d7c05f33a23f1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563813B2

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