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Benzylamine → 2-(Tert-butoxycarbonylamino)-4-methylthiazole-5-carboxylic acid benzylamide

HRID 45396
ノート
印刷プレビュー

反応式

HRID 45396 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:15]([OH:17])=O)=[C:12]([CH3:14])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(NC(C)C)(C)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:47]([NH2:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>ClCCl.C(OCC)(=O)C>[CH2:47]([NH:54][C:15]([C:11]1[S:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[N:13][C:12]=1[CH3:14])=[O:17])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 7504BenzylamineHCID 7912DiisopropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756770N-Boc-amino-4-methylthiazole-5-carboxylic acid

生成物 1

HCID 866425212-(Tert-butoxycarbonylamino)-4-methylthiazole-5-carboxylic acid benzylamide
収率 50.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2-(tert-butoxycarbonylamino)-4-methylthiazole-5-carboxylic acid (2.97 g, 11.50 mmol) and diisopropylamine (8.5 mL, 48.70 mmol) in dichloromethane (40 mL) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.25 g, 11.50 mmol) and 1-hydroxybenzotriazole (2.02 g, 14.80 mmol). After 30 min benzylamine (1.7 mL, 15.60 mmol) was added. The resultant mixture was stirred at ambient temperature over 8 h, diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford 2-(tert-butoxycarbonylamino)-4-methylthiazole-5-carboxylic acid benzylamide (2.00 g, 50% yield).

後処理

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography
  6. washeluting with ethyl acetate/hexanes (5/95 to 100/0)

出典と根拠

ORDレコード
ord-a0ca25b0155045efa99fa0e55e339a4f
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08541457B2

反応ノート

読み込み中…

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