Triphenylphosphine → 3-[(Benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]-6-methylpyridine-2-carboxylic acid isopropyl ester

反応式

[CH3:1]OC(C1C(O)=C2C(C=CC=N2)=CN=1)=O.[CH:16]([O:19][C:20]([C:22]1[C:27]([CH2:28][N:29]([S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:37])=[O:36])[CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=[CH:24][N:23]=1)=[O:21])([CH3:18])[CH3:17].N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(OC(C1C(CO)=CC=C(C)N=1)=O)(C)C.COC(=O)CNS(C1C=CC=CC=1)(=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH:16]([O:19][C:20]([C:22]1[C:27]([CH2:28][N:29]([S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:37])=[O:36])[CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=[C:24]([CH3:1])[N:23]=1)=[O:21])([CH3:18])[CH3:17]

参加物

実験手順

According to the conditions reported by Anthony et al (WO 02/30931 A2) for the preparation of 3-[(benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]pyridine-2-carboxylic acid isopropyl ester, a solution of diisopropyl azodicarboxylate (1.07 g, 5.30 mmol) in THF (5 mL) was added dropwise over 40 min to a stirred solution of 3-hydroxymethyl-6-methyl-pyridine-2-carboxylic acid isopropyl ester (739 mg, 3.53 mmol), N-(phenylsulphonyl)glycine methyl ester (810 mg, 3.53 mmol) and triphenylphosphine (1.39 g, 5.30 mol) in THF (15 mL) The resulting solution was then left to stir at room temperature overnight. The reaction mixture was concentrated to give crude 3-[(benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]-6-methylpyridine-2-carboxylic acid isopropyl ester as a golden syrup. This was used in the subsequent step without further purification.—Selected 1H NMR (CDCl3): δ 4.73 (s, 2H), 4.00 (s, 2H), 3.54 (s, 3H), 2.70 (s, 3H).

後処理

waitwas then left
concentrationThe reaction mixture was concentrated

出典と根拠

ORDレコード: ord-01e92db21a91481eb6791b12a3991f55
出典データセット: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07692011B2

反応ノート

読み込み中…

反応式

参加物

反応物 6

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

反応ノート