Triethylamine → 6-Methyl-2-oxo-4-(phenylmethyl)-3-[[(phenylmethyl)sulphonyl]amino]-1,2-dihydropyridine-1acetic Acid

HRID 1069428Notes

Reaction equation

HRID 1069428 reaction equation
C(N(CC)CC)C.[C:8]1([CH2:14][S:15](Cl)(=[O:17])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:19][C:20]1[C:21](=[O:39])[N:22]([CH2:34][C:35]([O:37]C)=[O:36])[C:23]([CH3:33])=[CH:24][C:25]=1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[CH3:33][C:23]1[N:22]([CH2:34][C:35]([OH:37])=[O:36])[C:21](=[O:39])[C:20]([NH:19][S:15]([CH2:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:17])=[O:16])=[C:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 15858475Methyl 3-Amino-6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydropyridine-1-acetate

Product 1

HCID 155467606-Methyl-2-oxo-4-(phenylmethyl)-3-[[(phenylmethyl)sulphonyl]amino]-1,2-dihydropyridine-1acetic AcidYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml (7.17 mmol) of triethylamine and 0.95 g (5 mmol) of (phenylmethyl)sulphonyl chloride are added to 1 g (3.5 mmol) of methyl 3-amino-6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydropyridine-1-acetate in solution in 30 ml of dichloromethane and the mixture is kept stirred for 12 hours at room temperature. The reaction medium is washed successively with 10 ml of water, 10 ml of a 1 N aqueous hydrochloric acid solution and then 10 ml of a saturated sodium chloride solution. The medium is dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a silica gel column, eluting with a dichloromethane:methanol (98:2) mixture. The product is used as such in the hydrolysis stage which is carried out according to the procedure described in Example 3. 0.8 g of product is obtained in the form of a white powder.

Workup

  1. washThe reaction medium is washed successively with 10 ml of water, 10 ml of a 1 N aqueous hydrochloric acid solution
  2. dry with materialThe medium is dried over magnesium sulphate
  3. customevaporated
  4. customThe residue is purified by chromatography on a silica gel column
  5. washeluting with a dichloromethane:methanol (98:2) mixture
  6. customsuch in the hydrolysis stage which

Sources & evidence

ORD record
ord-b6e2874a73304385b05b4d2a96caa06e
Source dataset
uspto-grants-2001_06
Patent number
US06252082B1

Reaction notes

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