Diisopropylethylamine → Tert-butyl 5-(methylcarbamoyl)thiazol-2-ylcarbamate

HRID 1874007노트

반응식

HRID 1874007 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:14]([OH:16])=O)=[CH:12][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:19]1[C:23]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN>C(#N)C>[CH3:23][NH:19][C:14]([C:11]1[S:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:13][CH:12]=1)=[O:16]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 222714422-N-Boc-Amino-Thiazole-5-Carboxylic Acid

생성물 1

HCID 86649520Tert-butyl 5-(methylcarbamoyl)thiazol-2-ylcarbamate수율 73%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a heterogeneous mixture of 2-(tert-butoxycarbonylamino)thiazole-5-carboxylic acid (1.0 g, 4.1 mmol), 1-hydroxybenzotriazole hydrate (0.63 g, 4.1 mmol), N,N-diisopropylethylamine (4.3 mL, 24 mmol), methylamine hydrochloride (0.83 g, 12 mmol) in anhydrous acetonitrile (20 mL), was added WSCDI (2.4 g, 12 mmol) at room temperature under a nitrogen atmosphere and stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. To the residue was added saturated aqueous sodium bicarbonate solution (20 mL), ethyl acetate (6 mL), and heptane (2 mL). The solid that separates out was filtered, washed with water (2×2 mL) and diethyl ether (2×4 mL), and dried to give tert-butyl 5-(methylcarbamoyl)thiazol-2-ylcarbamate (0.77 g, 73% yield) as a white solid. MS found: (M+H)+=258; 1H NMR (400 MHz, methanol-d4) δ ppm 7.83 (s, 1H), 2.87 (s, 3H), 1.55 (s, 9H).

후처리

  1. additionwas added WSCDI (2.4 g, 12 mmol) at room temperature under a nitrogen atmosphere
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionTo the residue was added saturated aqueous sodium bicarbonate solution (20 mL), ethyl acetate (6 mL), and heptane (2 mL)
  4. filtrationThe solid that separates out was filtered
  5. washwashed with water (2×2 mL) and diethyl ether (2×4 mL)
  6. customdried

출처 및 근거

ORD 기록
ord-4b75c05436cc4bc0a166d7589795cc22
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304539B2

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