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

HRID 640807Notes

Reaction equation

HRID 640807 reaction equation
[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]

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5149288N-(Phenylsulfonyl)glycine Methyl EsterHCID 22346294Methyl 8-hydroxy-1,6-naphthyridine-7-carboxylateHCID 592565463-Hydroxymethyl-6-methyl-pyridine-2-carboxylic acid isopropyl esterHCID 685642743-[(Benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]pyridine-2-carboxylic acid isopropyl ester

Product 1

HCID 592566753-[(Benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]-6-methylpyridine-2-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  1. waitwas then left
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-01e92db21a91481eb6791b12a3991f55
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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