2-Aminothiazole → Methyl 4-[(thiazol-2-ylamino)acetyloxy]benzoate

HRID 583692ノート

反応式

HRID 583692 の反応式
[C:1]([CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)(O)=O.C(Cl)(=O)C(Cl)=[O:18].[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1.CCN(C(C)C)C(C)C>C1C=CC=CC=1.CN(C=O)C.CCOC(C)=O>[S:24]1[CH:25]=[CH:26][N:27]=[C:23]1[NH:22][CH2:1][C:4]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=1)=[O:18]

参加物

8

反応物 4

HCID 21552-AminothiazoleHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 138161514-(Carboxymethoxy)-benzoic acid 1-methyl ester

生成物 1

HCID 18928580Methyl 4-[(thiazol-2-ylamino)acetyloxy]benzoate

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Acid 24-2 (1.0 g, 5 mmol) was suspended in 25 mL benzene, a few drops of DMF were added, then oxalyl chloride (1.3 ml, 15 mmol) in two portions. Once the gas evolution stopped, the homogeneous solution was concentrated, diluted with 25 mL DMF, and treated with 2-aminothiazole (550 mg, 5.5 mmol) and DIPEA (1 mL, 5.7 mmol). This mixture was stirred for 16 h, diluted with EtOAc, washed with water, sat. NaHCO3, and brine, dried (MgSO4) and concentrated providing 24-3 as an orange solid.

後処理

  1. concentrationthe homogeneous solution was concentrated
  2. additiondiluted with 25 mL DMF
  3. washwashed with water, sat. NaHCO3, and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8ef48a2f7b9342e4b446478ecb3d2f2d
出典データセット
uspto-grants-1999_07
特許番号
US05929120

反応ノート

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