Methanol → 3-(Benzothiazol-6-ylamino)-butyric acid

HRID 80217

反応式

HRID 80217 の反応式
C([O:3][C:4](=[O:9])[CH2:5][CH:6]([NH2:8])[CH3:7])C.I[C:11]1[CH:19]=[CH:18][C:14]2[N:15]=[CH:16][S:17][C:13]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CO>CN(C=O)C.C(Cl)(Cl)Cl.[Cu](I)I>[S:17]1[C:13]2[CH:12]=[C:11]([NH:8][CH:6]([CH3:7])[CH2:5][C:4]([OH:3])=[O:9])[CH:19]=[CH:18][C:14]=2[N:15]=[CH:16]1

参加物

8

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 98103Ethyl 3-aminobutyrateHCID 226090026-Iodo-1,3-benzothiazole

生成物 1

HCID 596361913-(Benzothiazol-6-ylamino)-butyric acid収率 22.22%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

3-Amino-butyric acid ethyl ester (2 g, 15.27 mmol), 6-iodo-benzothiazole (3.98 g. 15.27 mmol) and potassium carbonate (5.27 g, 38.18 mmol) were dissolved in DMF (50 mL) and the reaction mixture was purged with argon for 10 minutes. This was followed by the addition of copper iodide (290 mg, 1.527 mmol) and the resulting mixture was heated to 110° C. overnight. The reaction was monitored by TLC (10% MeOH in CHCl3) which showed the presence of starting material. The reaction mixture was heated to 120° C. for a further 24 hours. The reaction mixture was concentrated and adjusted the pH to 5 using acetic acid. The reaction mixture was partitioned between water and ethylacetate. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 800 mg of the product (22.22% yield).

後処理

  1. customthe reaction mixture was purged with argon for 10 minutes
  2. temperatureThe reaction mixture was heated to 120° C. for a further 24 hours
  3. concentrationThe reaction mixture was concentrated
  4. customThe reaction mixture was partitioned between water and ethylacetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (1% MeOH in CHCl3)

出典と根拠

ORDレコード
ord-1bff1dbf7917497a89502f5a5837242e
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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