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

HRID 583692노트

반응식

HRID 583692 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ef48a2f7b9342e4b446478ecb3d2f2d
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929120

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