Triethylamine → tert-Butyl 2-(5-formylthiophene-2-carboxamido)phenylcarbamate

HRID 416298

反応式

HRID 416298 の反応式
[CH:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][CH:4]=1)=[O:2].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH:1]([C:3]1[S:7][C:6]([C:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:10])=[CH:5][CH:4]=1)=[O:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 8188825-Formyl-2-thiophenecarboxylic Acid

生成物 1

HCID 58930645tert-Butyl 2-(5-formylthiophene-2-carboxamido)phenylcarbamate収率 33.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 5-formylthiophene-2-carboxylic acid (350 mg, 2.24 mmol), tert-butyl 2-aminophenylcarbamate (467 mg, 2.24 mmol) and triethylamine (470 μL, 340 mg, 3.36 mmol) and BOP (1.1 g, 2.68 mmol) in DMF (10 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated and purified by flash chromatography using 25% EtOAc in hexanes as an eluent, yielding 260 mg (33%) of the title compound. 1H NMR (CDCl3) 9.95 (s, 1H), 9.7 (br. s, 1H), 7.84 (d, 1H, J=8.0 Hz), 7.74 (m, 2H), 7.15 (m, 2H), 6.72 (s, 1H), 1.56 (s, 9H). LRMS: (calc) 346.1; (found) 369.1 (M+Na)

後処理

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-ee460b9b649d4ae1a10c3f119c93cbb9
出典データセット
uspto-grants-2012_01
特許番号
US08088805B2

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