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

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[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]

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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).

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waitwas then left
concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록: ord-01e92db21a91481eb6791b12a3991f55
출처 데이터셋: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07692011B2

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