Triethylamine → tert-Butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 1506581ノート

反応式

HRID 1506581 の反応式
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[S:22][CH:23]=[C:24]([C:26]([OH:28])=O)[N:25]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[Cl-].[CH3:30][O:31][NH2+:32][CH3:33].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1.O>[CH3:30][O:31][N:32]([CH3:33])[C:26]([C:24]1[N:25]=[C:21]([CH:18]2[CH2:17][CH2:16][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:20][CH2:19]2)[S:22][CH:23]=1)=[O:28]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27955312-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)-1,3-thiazole-4-carboxylic acidHCID 11040634Methoxy(methyl)azanium;chloride

生成物 1

HCID 86660504tert-Butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

At room temperature, triethylamine (324 mg) was added to a suspension of 2-[1-(tert-butoxycarbonyl)piperidin-4-yl]-1,3-thiazole-4-carboxylic acid (1.0 g) in dichloromethane (30 mL). After ten minutes of stirring, methoxy(methyl)ammonium chloride (312 mg), 4-dimethylaminopyridine (39 mg) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide HCl salt (675 mg) were added. The mixture was stirred at room temperature overnight, and water was then added. The aqueous phase was separated off and extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue was purified chromatographically. This gave tert-butyl 4-{4-[methoxy(methyl)carbamoyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.0 g).

後処理

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe aqueous phase was separated off
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified chromatographically

出典と根拠

ORDレコード
ord-f281a30edde24716bd2b286273c1e54d
出典データセット
uspto-grants-2015_12
特許番号
US09220266B2

反応ノート

読み込み中…