Hydrochloric Acid → N2-(3-chloro-2-methylphenyl)-N2-{[4-(hydroxymethyl)phenyl]sulfonyl}-N-(4-methoxybenzyl)glycinamide

HRID 1009485Notes

Reaction equation

HRID 1009485 reaction equation
[Cl:1][C:2]1[C:3]([CH3:34])=[C:4]([N:8]([CH2:21][C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[O:23])[S:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.ClC(OCC)=O.[BH4-].[Na+].Cl>C1COCC1.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]([CH3:34])=[C:4]([N:8]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH2:16][OH:17])=[CH:19][CH:20]=2)(=[O:11])=[O:10])[CH2:21][C:22]([NH:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 673045834-[((3-Chloro-2-methylphenyl){2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)sulfonyl]benzoic acid

Product 1

HCID 58009699N2-(3-chloro-2-methylphenyl)-N2-{[4-(hydroxymethyl)phenyl]sulfonyl}-N-(4-methoxybenzyl)glycinamideYield 40.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

300 mg of 4-[((3-chloro-2-methylphenyl){2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)sulfonyl]benzoic acid was dissolved in 5.00 mL of THF, and 340 mg of ethyl chloroformate and 326 mg of triethylamine were added thereto, followed by stirring at room temperature for 1 hour. To the reaction liquid was added dropwise an aqueous solution (0.80 mL) of 360 mg of sodium borohydride over 30 minutes, followed by stirring at room temperature for 2 hours. The reaction liquid was acidified with addition of 8.0 mL of 1 M hydrochloric acid, and then extracted with a mixed solvent of chloroform/methanol (5/1), and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10) to obtain a product, which was crystallized from diisopropyl ether to obtain 118 mg of N2-(3-chloro-2-methylphenyl)-N2-{[4-(hydroxymethyl)phenyl]sulfonyl}-N-(4-methoxybenzyl)glycinamide.

Workup

  1. customTo the reaction liquid
  2. stirringby stirring at room temperature for 2 hours
  3. customThe reaction liquid
  4. extractionextracted with a mixed solvent of chloroform/methanol (5/1)
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10)
  8. customto obtain a product, which
  9. customwas crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-120226161ea640b0bf4eff3e8ee7a028
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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