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

HRID 1874007ノート

反応式

HRID 1874007 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4b75c05436cc4bc0a166d7589795cc22
出典データセット
uspto-grants-2012_11
特許番号
US08304539B2

反応ノート

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